Looking Back

This is the first in a series of stories in which a successful business woman looks back on her life and asks herself whether she is a slut. In each story she tells, in the italicized portion of the story, a tale of one of her more memorable sexual experiences. If you just want the sex, skip to the part of each story in italics.

*****

2010

"I'm 60 years old, and I'm a slut," I said quietly to myself. I leaned back in a favorite armchair in a bedroom of my home in the Pacific Heights district of San Francisco. "Katherine O'Riley, you are a slut and have been one since you were about seventeen." I took a sip of wine and contemplated what I had just said.

The wine was exquisite, a ten year old Grand Cru Burgundy (an Aloxe-Corton, Clos du Roi, for those of you with a passion for detail), retrieved from my wine cellar earlier in the day and opened to breathe before I went out to an early dinner with a few friends to celebrate my birthday. I had restrained my drinking at dinner, knowing that I had this stunning bottle of Burgundy awaiting me at home. I let the wine swirl about my mouth as I savored the complex fruit flavors and then the subtle tannins, subdued by ten years of aging, first in French oak and then the bottle. Marvelous, I thought. A great bottle of wine is one of the best birthday presents you can give yourself.

Now there was nothing particularly troubling to me about being sixty years old. Thanks to a regular exercise program, I was still reasonably fit and trim, and according to my most recent physical, none of the customary diseases of aging had set in yet. I was still working full time as the owner and general manager of a small independent publishing company, Dark Secrets Publishing. I learned the trade working for one of the major publishing houses, but I love owning my own shop. We specialize in erotic materials, which are a hot item these days. I get along well with the people who work for me and with the authors and booksellers I deal with. I've even learned to put up with Amazon—a necessary evil in the book publishing business. Unlike others I know who have grown tired of their careers, I still thoroughly enjoy my work. Maybe it's because I publish dirty books, I told myself with a small giggle. I'm told I have a delightful laugh.

I stood, setting my wine glass on a table, and slowly stripped off my clothes. After another sip of wine, I stepped naked before a floor-to-ceiling mirror. Not bad for an old broad, I thought. My 34C breasts, while no longer "perky," still set nicely on my chest without the appalling sag most women my age have. My belly, albeit a bit softer than it had been forty years ago, was still trim and easily defined a waistline above my hips. My hips, always a bit broader than I would have liked and now even a bit broader than they had been, were still tight without the flab and cellulite of old age. I turned quickly, looking over my shoulder to examine my ass. A little rounder than it had been at twenty-five, but still what many men, including some I knew well, would call "a nice ass," with no appreciable sag. I sipped a bit more wine as I appraised my legs. Long enough to give me my overall height of 5'-8" and, thanks to my regular running program, they remained lean and hard. My hair was shoulder length and thick, a glossy raven in its current incarnation. I was determined not to let any gray show. My hair had been through a lot of different colors and styles over the years, but I had to admit, I was never totally satisfied with any of them, especially the mousy brown I had grown up with. Ah well, changing hair colors is a woman's prerogative.

I took another mouthful of the Corton. "Oh my," I said aloud in response to the nuanced flavors of the wine. Then I smiled as I thought of one more item on my list of accomplishments: "Oh, and I still thoroughly enjoy sex," I said aloud. I knew so many women my age who have long ago given up sex. "What fools these mortals be," I quoted, smiling as I sat down, still naked, in an armchair. All in all I thought, given that I had always assumed I would never live this long, getting to sixty is something of an accomplishment. I crossed my legs, continuing to appraise myself in the mirror, while reaching for the bottle on the adjoining table to refill my waning glass. "Yes, Kate (I go by Kate rather than the more formal Katherine. Only my Mother called me Katherine, and then it was usually when I was in trouble), all things considered you're looking pretty damned good."

The new idea was this business of being a slut. "Really? A slut?" I asked myself. Well, I had to admit that I seriously enjoyed sex. I had enjoyed sex from the time I passed puberty, and I still enjoy it today. And while I had eventually learned to occasionally say, "no," I never felt it necessary to do that all the time. But that doesn't make me a slut does it? "No, of course not," I told myself. I took another sip of the exquisite Corton.

But, I thought . . . I've been married four times. No, none of the three failures were my fault (except maybe the second). The first one had wandered off, ostensibly to "find himself," but never to return, so I divorced him after a couple of years of marriage in absentia.

The second had kicked me out when he caught me screwing his best friend, calling me a slut. I demurred on the issue of whether my bedmate was actually his best friend, or even a friend at all, and also to his characterization of me as a slut. But this evening, as I looked back over my life, it occurred to me that he might have had a valid point on the slut business. In any case, I made the divorce as easy as possible for him. He wasn't that good in bed anyhow, and he certainly wasn't going to be easy to live with after discovery of my affair with his "best friend."

The third died (fortunately leaving me a lot of money). I know one should be scarred for life when a spouse dies prematurely, but I had barely been married to him long enough to resolve such basic issues as who slept on which side of the bed, so I didn't feel a soul-crushing loss when he drove his sports car off a cliff after consuming the better part of a fifth of bourbon. I miss him though, I thought. He was such fun—both in and out of bed.

The second of my marriage failures was the only one I felt even a modicum of responsibility for. Given that I had cheated regularly during all of my marriages (including my current one), the only distinction in the second failed marriage was that I got caught. Luck of the draw, I always told myself. Of course, getting caught cheating during the third marriage and the current one was not an issue, given that it was explicitly understood by both parties to each of the marriages that the other would from time to time have a fling with someone else.

I'm still married to my fourth husband, Henry, but it is a marriage that hardly conforms to society's customary standards. We met in our early fifties via what I expected to be a classic one-night stand, but it didn't turn out that way. The sex that night was fantastic. Okay, maybe it really wasn't anything out of the ordinary. Maybe we were both just horny and hard up, so we thought it was something extraordinary. I learned years ago that the quality of most sexual encounters is as much a matter of perception as reality.

In any case it was good enough so that we extended our stay in the New York hotel room he had planned to occupy for just one night for another five days before returning to our respective homes (London for him and San Francisco for me). During those five days we not only learned a great deal about the others' sexual kinks, but discovered that we were really quite well matched (beyond just our sexual personas). When we weren't screwing, and at that age there was quite a bit of the five days when we weren't screwing, we just hit it off. Like me, he had been married three times, and we were greatly entertained by describing the challenges, trials, tribulations, successes, and failures of our prior relationships. He apparently had cheated as much as I had.

He is also a bit of a foodie, which nicely matches my fondness for fine wines. Neither of us holds any political persuasion with any passion. Although he is probably a bit more conservative than me (it's hard to be conservative if you have lived most of your life in Berkeley and San Francisco), neither of us really gives a damn about politics beyond the basic thought that 99 out of 100 politicians are lying scoundrels and egomaniacs. Really, who in his (or her) right mind would want to be President or Prime Minister? The job doesn't pay well, you have to be surrounded by armed guards all the time to protect you from the odd crazed homicidal maniac, and the press works overtime trying to think of bad things to say about you. Publishing porn is a much nicer occupation. These days you are almost a respectable citizen and much less likely to be indicted than a politician is. And if you know what you are doing, it pays pretty well.

After our lost week in New York we corresponded, by e-mail and otherwise (Henry still likes to write letters and send them by snail mail and he refuses to read digital books. How quaint.), talked by phone, including some really obscene phone sex, and created excuses to make business trips to mutually convenient destinations (frequently New York) for multi-day re-creations of our first "one night stand." One evening, somewhere around two a.m. as I was sliding from post-coital bliss towards sleep, I heard him ask me to marry him.

"What!" I responded, suddenly wide-awake. "Did you say what I think you said?"

"What do you think I said?" he asked.

"I think you asked me to marry you."

"I did."

"Really? You want to try again after three failures, and you want to try it with a woman who has also had three strikeouts?"

"Absolutely," he said. "I've always enjoyed being married. I enjoyed my relationship with each and every one of my former wives. They were lovely ladies."

"So what happened?"

"Well, they just couldn't understand and tolerate my habit of screwing other women. I wasn't prepared to give that habit up, or frankly, even capable of giving it up, so we had to move on with our lives."

"You, on the other hand, should be perfectly comfortable with that aspect of me. Given your lifelong habit of extramarital sex, I should think you wouldn't have any problem with it at all."

We talked until nearly 5:00 a.m. and negotiated the terms of what is euphemistically referred to in society today as an "open marriage," although looking back on it, I think it might be better characterized as a financial merger. He continued to live in London and I in San Francisco for good and valid financial and professional reasons in each case. Our principal concessions to our marital status were a jointly purchased loft apartment in New York (a very nice one I might add) and mutual tolerance of resulting significant incremental complexity in our tax returns. Yes, there was a lot of sex involved, but that would have happened with or without the marriage.

I still have my friends in San Francisco and he still has his in London. We talk almost nightly by phone (although the time zones do complicate the process a bit. "Daily" might be a better way to characterize our schedule, so long as you think of a day as a 24-hour period, plus or minus five or six hours), and we acknowledge that each has his or her own dalliances from time to time, some of which we take delight in sharing with the other. He really can be a wicked man and, like my second husband, he calls me a slut. But he does it on a regular basis, usually while we are fucking or having phone sex, so I have never taken it too seriously.

Until tonight that is. I had always thought of his characterization of my sexual habits more as a peculiar term of endearment, but tonight, for some reason, totally unrelated to my spouse's statements, it had occurred to me as I contemplated my major event birthday with a bottle of fine wine, that perhaps I was in reality a slut. I refilled my glass and held it before me, noting the dark red of the wine and the "legs" created on the wine glass when swirled, as I talked to myself about the question of my "slutdom":

"So what makes you think you are a slut," I asked myself.

"How many men have you slept with?" I responded.

I laughed and took another sip of the wine. "Since when?"

"Since forever. Like since you passed puberty."

"You mean like when I was in high school?"

"Yeah sure. How many men have you slept with since that first time when you were in high school? Or did you start earlier?"

"Hey, I'm not that bad. I may be a slut, but I'm not Lolita."

"Okay, but you haven't answered the question. How many men have you slept with?"

"Doesn't count if we didn't fall asleep afterwards, right? That's not 'sleeping together'," I asked myself, trying to dodge what I knew to be the obvious intent of my own question.

"Of course it does. How many men did you screw?"

"So blow jobs don't count?" I told myself, still prevaricating.

"Of course they do, and so do hand jobs, for him and for you, and so does cunnilingus. Even mutual masturbation in person, on the phone, or via the Internet counts. Oh, and by the way, so does sex with women. You know, you are beginning to sound like Bill Clinton with all this lawyerly weaseling."

"Okay. I got it."

It really is hard to have that kind of debate with yourself, I acknowledged. I took another sip from my wine glass as I thought about it. Damn, this was good wine.

"You know," I said aloud after thinking for a few moments about the question. "I really have no fucking idea how many people I've had sex with."

"More than twenty-five?"

I laughed. "Oh fuck yes! I don't know, but it's got to be way more than twenty-five. I've been screwing for forty-five years, more or less."

"So you are a slut then!"

"Yeah, I guess so," I told myself, "but you have to admit, it sure as hell has been fun." I laughed and took another sip of wine.

"Oh yes, that's for sure," I responded, finally agreeing with myself.

I noticed that the bottle of wine was at least half empty. "I'm going to have a headache tomorrow," I said as I poured another glass. This really was a great wine.

Then I got this idea to try to make a list of every man (and woman) I had ever had sex with. Of course I couldn't do it, but I was surprised at how many I could remember and how vivid some of my memories were.

Just then the phone rang. It was Henry.

"Hello."

"Kate? Henry here. Happy birthday. How's my favorite horny little slut. Not too traumatized by turning sixty, I hope."

No, sixty's not a problem at all, but the funniest thing happened this evening."

"What's that, lover?"

"Well, as I said, sixty is fine, but I also decided that I really have been a slut for the last forty-five years."

To his credit, Henry didn't try to argue with my conclusion. He simply asked, "How did you reach that conclusion?"

"Well, I was enjoying a really fine bottle of Aloxe-Corton, wishing you were here, and for no good reason I asked myself how many people I have had sex with."

"Didn't like the answer?"

"Worse than that. I didn't know the answer."

"Is that bad? It doesn't seem so to me. I doubt if I could recall all of the people I have screwed."

I laughed. "I love you," I said.

"Really. I mean it," he said. "Wait while I refill my coffee cup and you can tell me about them."

"All of them?"

"Well, perhaps just the memorable ones."

He set the phone down and I heard his heels clicking as he walked from his home office to his kitchen and back. Then I heard a long slurp as he sucked in a bit of coffee and he came back on the line. "Now tell me about them, Kate. Who was the first, and was he any good?"

"Really Henry? You want to hear about all of them now? We'll be up all night even if I just tell you about the best ones."

Henry laughed. "Yes dear, I suppose we would, although that's not such a problem here, as it's 6:00 a.m., and I just got up. I do really want to hear about them, but you're right. Not all of them in one call. How about just the first one tonight? Or today. These time zones make this the most confusing marriage I've ever had."

Now it was my turn to laugh as I thought about the first boy I ever had sex with. "Oh God no, Henry. That story is so boring. He was just this dumb friend of my cousin and he barely got it inside me before he went off. Then he got up and left and I had to finish myself off. It was a terrible introduction to sex, but there were others later, many others, that were so much better. I do want to tell you about one of them tonight. My pussy is getting wet just thinking about the man I have in mind."

"Do tell. Do tell. Far be it from me to keep you from telling me about sex so good it is still making you wet all these years later. Who was the guy? It was a guy wasn't it?

"Would it upset you if I told you it wasn't a guy?"

"No, of course not. I was just making a perhaps unwarranted assumption. So was it a girl?"

No. I'm just jerking you around. There was no girl involved, at least not directly."

"Really, a guy and an indirect girl. My dick is getting hard thinking about it, although the part about indirect sex with a girl is a little hard to fathom."

"She was just my motivation. Stop talking and I'll tell you about it."

"Please. I'll just drink my coffee while you talk."

I took another drink of the lovely red Burgundy as I thought about how to tell Henry about the "Pool Boy."

It was the summer after I graduated from high school. My friend Louise and I had jobs working as waitresses in a greasy spoon restaurant in Oakland, but we worked a shift that started at six in the evening, so we basically had all day to ourselves. Most days we spent a good part of it laying around my mother's pool in Orinda working on our tans. We each had bought ourselves about the skimpiest bikini we could find, and if no one was around we would sunbathe nude. Most of the time there was no one around because my mother had a job over the hill in Berkeley (and my father had left us for another woman years ago), so Louise and I spent a lot of time laying naked on the lounges around our pool that summer.

Now it's not like either of us were virgins. We had each had more than a couple of prior lovers, but as I was to learn from the Pool Boy that summer, the boys we had screwed were a poor excuse for sex. But the Pool Boy—he was a whole different story.

First the Pool Boy really wasn't a boy. He was very much a full-grown man, maybe thirty-five years old, which seemed ancient to us. He only worked for the pool cleaning company in the summer, and I think he was a P.E. teacher over in Oakland the rest of the year. He was tall, with broad shoulders and not an ounce of fat on him. When he came to clean the pool he usually wore a pair of relatively short shorts, a sleeveless t-shirt with the name of the pool cleaning company on it, and a pair of top siders.

This clothing did little to conceal the chiseled muscles that covered his body. He was tall, maybe 6'-2", with an olive complexion, further darkened by a serious tan. He had dark curly hair that was trimmed a bit shorter than was the custom in the early 1970s and, usually, about three days' worth of heavy beard. His eyes were striking. An icy blue, they could look right through you. I had talked to him briefly on earlier visits, and when he spoke to me, he looked right into my eyes like I was the only thing in his world. I can't tell you how many times I had masturbated that summer to thoughts of being ravished by the Pool Boy as he lay atop me staring into my very soul with his freaky blue eyes. He was so hot!