First impressions, again

Two women have presented me with a similar challenge, recently. Claire, with whom I stretched. Twice. And Shelby, whose face I fucked, whose clit I licked. Twice.

Both introduced themselves to me with disappointment, each, differently, demonstrating the kind of unreliability that I’ve come to associate, intellectually, cognitively, with a guarantee of future disappointment. And each, differently, also has demonstrated the capacity to please me, to give me precisely what I long for.

This conjunction – of the likelihood of disappointment and the possibility of gratification – exerts a powerful attraction over me. I hate it. I’ve gotten better at walking away from it over time, at minimizing the psychic cost of the disappointments such people inevitably bring me. But just as having been boosted lessens, but doesn’t eliminate, the risk presented by COVID, my evolution in consciousness may lessen both the likelihood and severity of my disappointment, but it doesn’t eliminate the risk.

Shelby, who has stood me up, cancelled on me at the last moment, disappeared, and interacted with me in ways different than I might prefer, continues to exert a powerful pull over my fantasies.

Though she’s presented me with all sorts of – if not incredible, at least unlikely – explanations for her cancellations and absences, I still find myself craving her pale thighs, her tiny waist, her round ass. Her warm, welcoming, mouth. Her longing to be restrained, to be spanked, to receive the punishments she’s earned.

I will note: five, seven, fifteen years ago? All of her disappearances and disappointments would have increased my longing. Today? Not so much. Today, I still crave her. But it’s just that: I still crave her. In spite of my craving’s having diminished somewhat in intensity.

Years ago, I would have been writing frantically about her, moving heaven and earth to persuade her of my desirability, of the attractiveness of what I have to offer. I would have obsessed. Would have lost sleep.

Today? I sleep well. I write less (about her). I simply note: I’m ready for her if, when, she reappears. I will delight, surely, in tying her up, in bruising her ass, in teasing her cunt. In feeding her my cock, in fucking her face. In teaching her how she should interact with me. I no longer have the fantasy either that I’ll succeed in teaching her, or even that she’ll grant me all I wish from her. I don’t think she will. I don’t think she can.

I do think, though, that in spite of her ambivalence – which has coursed through nearly every one of our interactions, in hesitancy, anxiety, and all the above-mentioned disappointments, disappearances, and so on – she knows that there’s some serious fun awaiting her, and that she will, when she’s ready, endeavor to collect that fun. Time will tell if I’m right about her. And, I suppose, if my ardor will wait. Hard to predict. But time will tell.

With Claire, it’s a bit different: with Claire, my relationship depends on money. I pay her to stretch with me. As a paid stretching partner, so far, at least, she sucks: she’s not reliable. She doesn’t turn up. If there weren’t a bit of another connection, a non-commercial, more fun connection, I would, surely, be done with her. But she does offer at least the possibility of some fun: her ski mask idea, for example, is pretty fucking excellent. And her magnificent, big ass – which initially she envisioned seeing on this blog, but then wanted to keep more private (as she told her friends about me, about my blog), may yet turn up here. Which would be nice. For all of us.

After her most recent flakery, I asked her, “How can you reassure me you’ll turn up next time? And how can you make up to me the disappointment you inflicted on me?” Claire isn’t creative in this way. She was fresh out of ideas. 

I offered some. A discount on our next session. Some photos for the blog. More photos, not for the blog. An orgasm. Two orgasms. 

And to reassure me? A deposit – she might send me some money, to be refunded – with pay – when she actually turns up for our next session. 

She’s been silent. Maybe pondering. Maybe not. The loss of Claire will not sting quite as much as the loss of Shelby already has: her mouth hasn’t engulfed, won’t engulf my cock. So the loss is less. But still… I would like her (back).

I would like them both back. 

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