Peak Experiences, Peak Fantasies

I’m in a bit of a relationship/sexuality jag, reading-wise, and right now, I’m reading The Erotic Mind, by Jack Morin. It’s a sort of pop-psychology guide to how to think about eroticism, desire, arousal, excitement, purporting to be a somewhat scientific study of people’s responses to a survey instrument. On the one hand, it’s clearly bad science: the survey methodology is, to use my grandmother’s term, verkakte, or crappy. On the other hand, that same grandmother also would have told me, “Just because you’re paranoid doesn’t mean people aren’t out to get you.” In other words, just because it isn’t rigorously scientific doesn’t mean it’s not informative or useful.

Morin’s theory is that we can learn a lot by looking at those experiences we hold above all others, those fantasies we cherish above all others – what he calls “peak” experiences and fantasies. This seems wise to me. And interesting. I wrote once, early on, about my greatest fantasy. One day soon, I’ll revisit that fantasy in the context of the thinking I’m doing right now, and in this post. Among other things, I have a vital improvement to the fantasy, one that renders it infinitely hotter to me. But in this post, I discuss not a fantasy, but an actual sexual experience.

If I’m honest, the hottest sexual experience I can remember is one that fills me with shame and regret, and that in some ways I wish I could strike from my past, and even from the realm of fantasy. It was toward the end of my lying days, and the peak of my loss of control. I was truly insatiable – there was no end to the money I could spend, the women whose presence I could command. I paid three women (as I recall, it was scheduled to be four, but one flaked at the last minute). They dressed as I requested – two, I asked to dress as if they were going out clubbing, in tiny black dresses, thigh-highs, pumps; one, I asked to wear jeans and a white t-shirt (I had a particular thing for her ass in jeans). I asked them all to wear boyshorts. And I asked each to bring a bag with several pairs of panties, several t-shirts, and a favorite toy or two.

I met them in a bar – not a ridiculously fancy place, but not a dive – a quiet, dark bar. I sat some distance from them for a bit, just watching them, enjoying seeing them enjoy one another’s company, admiring their faces and bodies, and savoring the anticipation of what lay before me. At some point, I texted them to join me at my table. They did. We sat together for some time – maybe one drink. I sent each of them, in succession, to the ladies room, with explicit instructions to play with herself for a bit, and not to wash her hands before returning. There may have been a tiny bit of teasing touching at the table, but I was self-conscious. My city, though a big one, actually is a small town, and I never once was in such a situation without being terrified of being seen.

At a certain point, I settled with the bar, and followed the three ladies out to a cab, again, savoring the anticipation as I watched them walk ahead of me. Into the cab, and once in, their instructions (delivered by e-mail or text in advance) were to play with themselves – the two in the back seat with me, at least – with one hand, and with the other, to rub my legs, my cock. We got to our hotel room, and I lined them up against a wall, asking them to bend over for me. I admired their asses, and then, had them kneel for me. One by one, I moved down the line, having each suck my cock briefly. Then, we adjourned to the bed, where I was somewhat passive, allowing two at a time to work on my cock while the third either sat on my face or, at my instruction, played with herself on a chair in a corner, or changed into a different panties/t-shirt combination.

I don’t want to glorify this scene, or to congratulate myself on bringing it about. It cost a ridiculous amount of money, and while I genuinely believe that each of these three women was happy to be with me, and not just to be paid, the point is, I paid. And the whole thing was flagrantly in violation of my vows to my wife, and all sorts of less formal, but no less vital, obligations.

The reason I’m writing about this is because I think there’s a lot of information about me in it. Because it was, essentially, a lived fantasy, and therefore, enormously informative about my desires. And because, if I’m honest, it was the hottest sexual experience I’ve ever had. (Note that my recounting of the fantasy stops long before my orgasm. It’s not the orgasm that makes the whole thing work; the orgasm is just the thing that brings it all to a conclusion.)

But why? What about it was so hot to me? Why did I construct the evening thus?

Why meet in a bar? Why direct their dressing? Why the two dresses? Why the jeans and the t-shirt? Why watch them at a distance? Why summon them by text? Why the one-by-one masturbation adjournments to the bathroom? Why not wash their hands? Why the specific instructions in the cab – the playing with themselves, the touching me? (And, not incidentally, why originally four, and why did the one flake? Was that itself even part of the fantasy?) It happens that this evening was not the first time I was with any of them – is that significant? (Many people’s hottest memories feature “firsts.”) Most important? Why is the hottest memory I have one for which I paid? Was the money itself central in some way?

Each step in this fantasy/event played a purpose, one to which I was almost entirely oblivious at the time, and to which I even now only have glancing insight into.

To begin with – the structure of the first part of the evening, meeting in a bar, them at the bar, me at a distance, them joining me: a fact about me is that I have picked up a woman in a bar exactly one time in my life. I was in my 20s. She was a waitress. In my late 30s, I came dangerously close once, at a bar in Chicago, on business, but I freaked her out at the last moment with my… enthusiasm (desperation?). And while we traded numbers, and texted a bit, we never actually hooked up. And another fact: I’ve fantasized a lot about picking women up. It’s just never been my M.O., for whatever reasons (most, I suspect, having to do with the ways in which, the circumstances in which, my confidence manifests, and those in which my insecurities do).

So there, in a bar, with beautiful women? I’d never approach them, never convert an ogling opportunity into an interaction (let alone a sexual encounter). And in this scenario? Not only did I use money to load the dice, but I didn’t choose to walk up to them at the bar and join them – what would most likely happen in any “normal” pick-up attempt. No, I chose to have them approach me, but to control how and when they did by text – a manner invisible to all but me and the one who received the text.

What’s this all about? One thought springs immediately to my mind: it’s like I created a great big piece of kabuki theater, in which to anyone looking, it would appear as if these three hot women came to me. Not like I was paying them, but rather, like they saw me and picked me out and came over to me. Another thought: that’s how it would appear to anyone looking, but I don’t think that this play was for anyone’s benefit other than mine. In other words, I don’t think I was hoping that some random guy at the bar might be impressed by all this; rather, it was almost as if wanted to believe this is what happened. (I don’t think I would have cared one way the other if there had been no one else in the bar or hundreds of people.)

So then, on to the next part of the fantasy: the one-by-one adjournment. Somehow, almost all of my fantasies feature women giving themselves pleasure. It’s as if by doing so, they’re providing tangible visible (and olfactory, even) evidence that pleasure is something they enjoy giving themselves, for their own sake. Even when I was a teenager, I remember being on an eternal – and almost entirely unsuccessful – search (given my access to porn in those pre-internet days) for images of women masturbating, penetrating themselves, touching themselves, with their fingers or with toys.

Never mind that, on this night, they were doing so at my instruction. I may be the director, but, as I established above, I’m also the audience, and I can play both roles simultaneously. I don’t know how I got in my head the thesis that women don’t want sexual pleasure, that to the extent they allow me to participate in it, they’re doing it as a favor to me and not in fulfillment of their own desires, but I crave constant, infinite reassurance on this subject. And not just behavioral reassurance – sensory reassurance, visual, olfactory. I think this is why I so enjoy watching a woman masturbate: if authentic, it’s irrefutable evidence of her being a sexual being in her own right, of her having her own desires, her own pleasures, and not simply conceding to mine. (Even if she is simply conceding to mine.)

Next? The clothes. Loyal readers will know by now that I love to direct the clothes a woman wears. Not only that, but my repertoire actually is quite limited. I like a woman in jeans. I like a woman in a skirt. I like a woman in a tiny black dress, or a sheer cotton one. I like a tight white t-shirt. I like boyshorts and briefs. Thongs? Not so much, except in pictures. I like panties over commando. I’m not a big fan of bras. And I love a baseball cap. Heels? Sure, if they go with the outfit, but not necessary. What the fuck is this all about?

When I go to strip clubs – something I used to do quite often, but now is an infrequent part of my repertoire of sexual activities – I always marveled at what we men seem to find exciting. At times, I’ve fantasized about opening a strip club (or a chain of strip clubs) that features women dressed like actual women, in actual clothes – casual clothes, work clothes, the clothes the women I interact with every day are wearing. This clearly is my aesthetic preference. Are there men who would prefer to see women wearing slinky long dresses that can be removed instantly? I guess most, but I’m not one.

But why the highly specific direction of the dressing? The only thing I can conclude is that it’s about control more than anything else – I want concrete, tangible, visual evidence of compliance, of acceptance of my wishes. And I want it in a way that’s evident to me even before we say hi. Even before we’re in the same place. Part of how my anticipation works is that, in the hour before we’re going to meet in a situation like this, I’d be imagining what the woman was doing, imagining her dressing, and might even ask her to send me photos of her on her way. And if I were paying hourly, I honestly should have been paying for that time too – it was every much as central to what I got out of encounters as the two or three hours of explicitly sexual activity.

And then, the cab: I’ve already covered what it is that seeing a woman masturbate does for me. Why the highly specific directions to touch me? I love a woman’s touch. I crave it. My shrink once theorized that my somewhat addictive consumption of “sensual massages” was a result of my desire for women’s touch being “accidentally erotized” by those massages, that I probably could have happily simply become “addicted” to legitimate massages given by women. When I was thirteen, sitting with my first girlfriend in a movie theater, I would secretly hope she might touch my leg, even as I touched hers. I would spend the entire movie perseverating on that hope. I would never dream of asking, of stating my preferences, or of guiding her hand where I wanted it. That dynamic was alive and well at 17, with my first college girlfriend, and it persisted, I’m embarrassed to say, well into my 30s with T. Maybe even into my 40s. So directing these women, women whom I was paying, who were working for me, to touch my leg, to stroke my cock – directing them in advance, without instruction in the moment, created a bit more theater: they were giving me what I desperately wanted, and doing so seemingly, apparently, of their own volition.

A pause: I wrote the other day, in my post on what I think about when receiving head, that I want inoculation in sexual encounters – I don’t want to have to “deliver” anything, and I actually want simply to give my partner/s what she/they want. Don’t get me wrong: I have specific things I’d like them to want. But I want it all to be fulfillment of their desires that is driving the agenda, not the fulfillment of mine. That’s somehow vitally important: I suspect my desires scare me somehow, whether because they’re powerful, or shameful, or annihilating, or violent, or what. But it feels much safer to me, much more arousing, if what I want is definitionally what my partner wants (hence my affinity for dominance).

Then, to the hotel room: the line of them, bent over, asses exposed to my touch, my view, and then mouths waiting for my cock. This seems like a straightforward demonstration of my power, of my “prowess” – these three women, bent over, then kneeling, vulnerable to me, submissive to my instruction? Evidence of the power I command as a man. Maybe this is some sort of perverse payback for anger I feel toward women; more likely, I think, just an overt demonstration of how powerless I actually felt (feel?) over women.

The structure of the sexual interactions – the fellatio ad infinitum, the oral ministration by me, the costume changes, the masturbation in the corner – all that’s just more of the same, no?

What of the absent fourth? In some way, she was essential: she was a reminder for me of my utter inability to control these women – I couldn’t even command their presence. The one who was absent was one with whom I had an ongoing “thing” for years, and who often flaked. It was as if, somehow, her flakery was part of her appeal.

And then, finally – the most important act of the evening? The rifling out of a stack of bills and sending (to send?) the women on their way. Charlie Sheen famously claimed not to have paid women to have sex, but rather, to have paid them to leave. I’m not so deluded. I believe the women had fun, but they were working. Many of us are lucky enough to have work or do work we enjoy. These three are among them, I believe.

But for me, that money played a truly vital role: it undermined the whole thing, reminded me that it was all theater, that, in fact, my desires had had nothing to do with what had just taken place, but that rather, it had been a trade, pure and simple: my money for their obeisance.

This was, I think, the most complicated part of the whole “peak experience” for me. On the one hand, it was the sine qua non for the whole evening (and for the whole fantasy part of the evening). It permitted the experience to happen, and it permitted me to be protected from the conclusion that in fact the women had been responsive to my desire (rather than to my money). On the other, it undid so much of the value I got from the evening.

This is the funny thing about how desire works, how the mind works. My conscious mind and my unconscious mind were warring with one another, and they produced an event that was simultaneously the hottest thing I can remember and the most shameful. No coincidence that, for sure.

None of this is intended to be presented as a “correct” interpretation of any of what happened. I remain mostly a mystery to myself, and welcome thoughts, opinions, observations, questions.

And also, shared peak experiences!


  1. i love this; when you write about your desire. when you try and pick apart your fantasies and experiences. it manages to be hot and smart at the same time. i would much rather read and write about this than the actual work for school i have to do today. after my final on wednesday, i wanna try and write about some of my own fantasies

  2. I like this so much? I guess its because it reminds me of myself and how i write. I’m always trying to pick apart my own mind. But I honestly feel like I could read this over and over again. I want more.

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