I’m not allowed to have this fantasy because it’s a fantasy about paying for sex. I both don’t love paying for sex, do love paying for sex, and don’t want to fantasize about paying for sex. But Margot is not available unless I pay, and I want Margot.
I don’t know that Margot is available in the ways and for the purposes I would like. I don’t know, for example, if she’ll dress as I ask, or if she’ll suck my cock without a condom, or if she’ll allow me to lick her clit and finger her, and maybe even fuck her. The truth is, I sort of imagine that that last option — the fucking — is the one that’s most likely to be on the table of all the others. I didn’t even mention kissing, which feels to me like a sine qua non for just about everything.
So in this fantasy, Margot is, in fact, available. Whatever the price is, it’s my fantasy, so the price isn’t that high. It’s more like a token than like real compensation. In this fantasy, the compensation works as I allowed myself to imagine compensation worked with Serena — which is to say, she needed to be able to tell herself that she was being paid, and that was the requirement. That is, in fact, how it was with Isabella, as I recall. At least once, she sucked my cock for $5, professing that being a $5 whore was at least as hot as being a $500 whore.
So here we are, Margot and I, approaching our first tryst. I suppose, most likely, it begins with a website by the same name — Tryst. I’ve never used Tryst, because I stopped seeing sex workers other than in massage parlors long, long ago. But I understand that Tryst is the contemporary equivalent of Eros, the website back in the early 2000s on which sex workers plied their trade most often, other than Craigslist. And I know Margot’s on Tryst because she told me, the last time I saw her, that she had spent the morning doing a photoshoot for what she described as her escort profile on Tryst.
In my experience, very few of the women who do sex work with whom I have had encounters have unabashedly described themselves as escorts or as doing escorting. I must have preferred even more euphemistic descriptions. But I was slightly both repulsed and cheered to hear Margot describe herself as escorting. On the plus side, I take it to mean that her limits are pretty flexible. On the minus side, I take it to mean that her limits are pretty flexible. I like to be special, or at least to imagine I am. If I’m just one among legions, that can make me feel especially bad in a context in which I start off feeling not so great.
Anyway, back to the forbidden fantasy.
I reach out to Margot by Tryst. I say: *Margot, I’ve been thinking about it, and I looked at your Tryst profile. Here’s what I want. Tell me if you’re interested.*
What I want is for you and me to meet one afternoon and to set aside several hours for mutual pleasure. I want to direct your clothing, your dressing. I’m not sure what this means in practice, other than that I’d like to select every item in which I will find you from among at least some choices. It could mean I’ll want to see you in jeans and a t-shirt, cotton panties, and a cotton bra. It could mean I’ll want to see you in a little black dress and fancy lingerie. I’m just not sure. But it will mean I have some preference that I’d like you to accommodate, to indulge.
My expectation would be that we would meet for a drink in a hotel bar, or a bar adjacent to a hotel. And then, after one or maybe two drinks, we would adjourn to my room — perhaps together, perhaps you first.
I don’t need to script precisely what will happen in that room. The way my fantasies go, what actually happens in the room is of far less import than everything I’ve described thus far. This isn’t to say it’s not important. It’s just to say it isn’t where the juice of this fantasy is for me.
The thing I can say for certain is that if you’re not interested in kissing me, if you’re not interested in sucking my cock without a condom, and if you’re not interested in allowing me to go down on you, to finger you, and perhaps to use a toy on you — then I think, alas, this fantasy is destined to remain just a fantasy. Because in the absence of those, I’m not so interested.
Which brings us to a second possible fantasy — one that might be more achievable.
Now you know what my fantasy is, what I’d like to do with you. If you’re not up for the task, or if it doesn’t appeal, or if for whatever reason it simply isn’t possible — fantasy number two has you providing someone who will do all this with and for me. It can’t be just anyone. I have some requirements.
She has to be personable. She has to be seductive. She has to excel at indulging, if not actually providing, a non-transactional experience within the context of a transaction. I’d prefer she be on the petite side — your height is at the top end; smaller would be better. She can’t have augmented breasts. I don’t care what size they are, but if they’re augmented, she’s the wrong woman for me. And she has to be down with everything I’ve expressed here so far, as well as with engaging in a little teasing, playful texting in the day or two prior to our tryst.
In this fantasy, the financial element is managed between you and me. I’ll hand you some cash or send it to you by Cash App. My date will not see a penny from me directly. She’ll allow me to imagine either that you gave her 100% of what I gave you, or that you gave her none of it, or something in between. Regardless, she’ll allow me to imagine that she’s with me because she wants to be, and that no clock is ticking. That I have her from, say, one to five.
Fantasy number three is a lot like fantasies one and two, except they’re combined. In this fantasy, not only do you procure and provide for me, not only do you manage the financial aspects of the transaction — but you’re a full-blooded participant alongside your companion.
I have other fantasies involving you. But for now, I’ll stop here.
Header image prompt (openai): Large-format color photograph, shot on 8×10 film with a single practitioner’s ring light mounted just below camera axis, casting a faint clinical halo that sits wrong against the warmth of the scene: a hotel bar’s leather stool holds a woman’s folded blazer and, beside it, two untouched whiskey glasses condensing in the late-afternoon amber light, one with a faint crescent of lipstick at the rim. The glasses are too close together, touching almost. The stool beside the blazer is empty but pulled out. Everything is perfectly, expensively still — and the ring light’s reflection floats in both glasses like a cold white eye watching back.