A date for another day

Diana and I made a plan.

Our relationship has been… attenuated. We stretched for a while together. We had a misunderstanding. We rectified it. We clarified things. We didn’t stretch together for a while. We stretched together again. And, after a lengthy break, we stretched together again. This time, Diana said to me, “I’m ready to spend an afternoon with you.”

We set a date, about a month in the future. Circumstances were such that there wouldn’t be a possibility for us to stretch but one time in that long, long wait. We did stretch together that one time. It was, characteristically, fun. Diana and I like one another. We get along well. We have good conversations. And, she’s motivating, and delightful to look at. At times (though not so much recently), she has enjoyed coming for me at the beginning or end of our sessions together.

Diana’s preferred way to get herself off is to sit atop a body pillow she has and to hump it feverishly. It doesn’t, typically, take her long. She grinds her body down on the pillow, and, shortly after starting, she almost silently shakes a bit, and stops. She finds it hard to maintain eye contact as she gyrates on the pillow, but she likes my voice, she likes to hear me talk to her while she’s stimulating her clit with pressure and friction and movement.

As our “date” approached, I thought it might make sense to touch base, to clarify. Diana’s libido has been all over the place since I’ve known her: at times, she’s been very horny; at others, completely without desire. Further, Diana pays her bills by “sugaring,” as she calls it – with relationships she has with three (primary) men who support her financially. I’ve been clear that “sugar” isn’t among the riches I offer. And she had been clear that, prior to her invitation to me, at least, the idea of traveling to have an uncompensated sexual encounter with me (we’re about an hour apart) just “wasn’t worth [her] time.” And I had been clear that the idea of traveling to have an uncompensated sexual encounter with her was worth my time.

So when Diana invited me to her place, I understood it as movement in our standoff, an openness to moving our relationship in a more explicitly sexual direction, without the sweetener of “sugar.” I wanted to be sure, though. I didn’t want there to be disappointment on either of our ends – on her part, to learn (again) that I wasn’t prepared to shift the commercial nature of our relationship; on mine, to learn that she wasn’t prepared to shift the sexual nature of our relationship.

I e-mailed Diana, expressing clearly my hopes (that I would get to bit her thick, creamy thighs; that I would direct her movements in person; that I would slide my cock in and out of her mouth, taste her cunt, and feel her orgasms), my expectations (that nothing was promised, but that nothing was off the table), and my fears (that she would be disappointed with my unwillingness to pay her).

Her response was comprehensive, thoughtful, and quick. She didn’t address the question of money, but rather, described the three relationships she currently maintains, how they are, for her, primarily emotional, how the sexual aspect of them is, at most, secondary, and maybe even tertiary. In her description, it sounded as if the sex is something she doesn’t look forward to, doesn’t want, and doesn’t see as being especially… important… in the relationships. Although yes, she had a date scheduled with one of those guys in the coming days – a date on which they would play tennis together, eat a meal together, chat extensively, and yes, have sex.

I responded to her that she and I are similar in some ways, and different, in others. Like Diana, I have zero interest in a sexual relationship that doesn’t have an emotional component. I need to like, to care about, to be interested in, the women with whom I have sex. (It is true that I’m capable of sexual interactions with strangers – a la Le Trapeze – but it’s also true that those encounters are rare, not especially gratifying, and unlikely to be repeated in the absence of an emotional and intellectual connection.) For Diana, it seems, sex is the price she has to pay for gratifying emotional connections, and the money is incidental, but helpful. For me, a man with a life full of family, friends, colleagues, acquaintances, and more, the emotional connections are vital, necessary, but they aren’t the point: I have enough of those. The point of the emotional connection for me is to lubricate, to make possible, the sexual connection. The point of the sexual connection for her is to facilitate, to punctuate, the emotional connection.

Diana told me that her libido hasn’t returned. She doesn’t have a lot of desire, generally; she doesn’t have a lot of desire, specifically, for me. Our emotional connection is nice, but it’s not on a par with those other relationships she has. We don’t chat on the phone, we don’t have a real connection that bridges our times together (such as they are). And, she doesn’t really have the time to invest in developing that at the moment. She left the door cautiously open to a shift, but was clear that, where she is right now, what I have to offer doesn’t compel her.

My conclusion was similar: I told her, the idea of traveling to see you if you don’t actively want my cock in your mouth, if you don’t actively want to give me what I want – well, that’s just not all that appealing to me.

So, we won’t meet any time soon. As I said, she left the door cautiously open: she hopes her libido will return. She has had a raging libido before; she expects to again. And she didn’t say it explicitly – that’s not really her style – but she made clear that she can imagine a universe in which her libido might align her wishes more with mine, that such a universe is possible, but not right now.

It’s all a shame, and yet, it’s all good.

Had I traveled to spend several hours with Diana, and we hadn’t had sex, I would’ve been disappointed. I don’t know the story she had been telling herself: maybe it had been that she would’ve had sex had I been prepared to help out with her rent. I don’t quite think that. But it might have been. I think, rather, that she hadn’t thought it all through when she invited me. That she knew my stance, and that she had hoped to be in a somewhat different place by the time our date rolled around – a different place both with respect to her libido and with respect to our emotional connection. In any event, we’re not where we would need to be for each of us to use the other for a mutually gratifying encounter. Or at least, to be where we would need to be for it to make sense for either of us to travel to the other.


For the record, here is what I had had in my mind as a “successful” version of our planned time together:

I arrive at Diana’s apartment. I’m carrying a bottle of wine juice for her. A bottle, or a flask, of scotch for me. Maybe some chocolates. She’s ordered in, or prepared, a light lunch for the two of us. She’s wearing the black dress in which I have so enjoyed watching her come. And a black lacy bra. And a bright pink thong. Or maybe, maybe, she’s wearing jeans. White panties. And a white bra. Yes – on second thought, that’s how I would dress her. Jeans. White t-shirt. White lingerie.

We would kiss hello – probably chastely. We would sit down, and I would pour us each a glass of our beverage. We would click our glasses together, and sit, and talk. And eat. And talk. And drink. And talk. Maybe 45 minutes or an hour into our conversation – conversation I would expect mostly to be not sexual – I might ask Diana to open her legs for me. To take off her t-shirt, to show me her gorgeous, big, round breasts in her bra. Conversation would continue, though, at this point, I imagine I might be fondling my cock, stroking it, as the conversation became more explicitly sexual, as I began to tell Diana just what I hoped she would do to, with, for me; just what I would do to, with, for her.

I would have her take off her bra. She would be sitting with me, topless, in jeans, as we finished off our lunch, as I admired her very curvy, very pale body. “Stand up,” I might say. “Turn around for me.” And she would, showing me her stellar ass in her jeans – a view no (straight) boy could help but find… stimulating. “Take off those jeans,” I would say. And she would, shaking her round ass in the pink thong in my face as she wiggled out of the jeans.

“Now, walk across the room,” I would instruct her, directing her to the furthest distance possible in her apartment from me. “And get down on your hands and knees, and crawl back toward me.”

I would watch Diana’s long, lustrous brown hair, her pretty dark eyes, her magnificent cleavage, as she would crawl across the floor to me. And when she reached me, I would say, firmly, kindly, softly: “Now, please get on your knees in front of me.” And she would. “Unzip my jeans,” I would say, “and tease my cock a bit.”

Diana would rub her hands on the insides of my thighs. She would stroke the growing bulge in my jeans, reaching in to grip my cock through my black cotton boxer briefs. I would ask her to back up a few inches, so I could stand. Together, we would get me out of my jeans, out of my boxer briefs, and I would drag my by-then-really-fucking-hard cock across her lips. I would grip her head at the back, grabbing a fistful of that shiny hair, and I would guide it slowly, slowly, to my cock, pressing my cock past her lips, into her mouth, and I would gently, forcefully, fuck her face, taking from her mouth the stimulation, the sensations, that I’ve craved from her for so long.

And then, then, after learning the contours of her mouth, the sensations it provides, I would direct her to her bed, to lie down, to open her legs for me. I would slide her panties over her thighs, her knees, her ankles, and would toss them to the side. Or maybe (if I’d gotten permission beforehand), I’d tear the panties off her with a single pull. Either way, her pussy would be splayed open before me, and I would continue the meal we had begun at her table, feasting, devouring, fingering, licking, flicking. I would slide my fingers in, I would press against her ass. I would sidle up, and press my hard cock against her pussy’s lips, maybe entering, maybe not. Maybe she would trust up to meet my cock. Maybe she would flinch just slightly backward, away from my cock.

In either case… from this point on, it’s hard to say what would happen. Would I loop my belt around her neck? Choke her a little? Fuck her hard? Probably not, any of those things. Would I spank her ass? Bruise her pale flesh? Direct her to perform a bit for me? More likely. My sense, from our chemistry, is that whatever would happen mostly would be a result of direction, that if we were dancing, I would be leading firmly, that she would be gamely following, but that her… hunger… would be implicit, not explicit.

No matter: I trust we both would have heaps of fun, that we both would feel we had spent our time well, by the time I collected a final orgasm from her, by the time I filled her mouth, or my condom, with cum, by the time we kissed good-bye, a little less chastely than we had kissed hello. And, that we would want to see one another again. And soon….

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