Note, and apology: I recorded myself dictating this post in a voice memo, and have edited it very (too) lightly. It reads a bit disorganized. When I write my book, this will be much more polished. 🙂
I was just thinking, it’s been a long time since I’ve had a threesome, and the last threesome I had, which was with Charlotte and Sarah, was delicious and fun, but there was at least one aspect of it lacking. Which is not to take anything away from either Charlotte, Sarah, or the threesome. But the aspect that was lacking was complete ease and comfort on everyone’s part. It was Sarah’s first threesome, it was Charlotte’s, well, not her first, but something close to her first, and each of them wasn’t really in a fully secure place in their relationship with me, and I wasn’t really in a fully secure place in my relationship with either of them. And not that any of that is ever fully possible, but it is, at least in my fantasies.
And so, here are a few things that, in my fantasy, I would love to happen in my next (as yet un-casted) threesome. I will say that I have experienced more or less of some of the things I’m about to say in some combination of previous threesomes, both commercial and non-commercial. In particular, I was able to protect myself and my partners from some of the discomfort that can come from anxiety or insecurity or discomfort. Or maybe I was able to protect myself from their anxiety and discomfort because of my paying. Or maybe it was just that the money protected me, and not that the discomfort wasn’t there.
Here’s one visual memory I have from a threesome I had with Willow and the party planner (a sexy young thing I could swear I’ve written about but, now, can’t find in a tag on the blog). I should say, the party planner introduced me to Willow, and Willow and I had a much longer-lasting relationship than I did with the party planner. But the party planner was a ton of fun and smoking hot. And the three of us had a number of threesomes – as well as some permutations that featured other women instead of, or in addition to, one or the other of these two….
What I really loved to do in those threesomes, and in all threesomes I would say, is to stage the arrival of the ladies. Which is to say, there’s something for me very exciting about a woman arriving, expecting to be engaged with me sexually, and finding me already engaged sexually with another woman. And with none of it being a surprise, with all of it being fully anticipated, foretold, predicted. In the particular instance I’m remembering, Willow and I went up to a hotel room, and the party planner arrived to find Willow on her knees with my cock in her mouth. The party planner walked around to kiss me hello, and she and I found space for our tongues in the other’s mouths while Willow continued expertly sucking my cock. [I will say about Willow that her mouth was a particular thing of beauty, both to kiss and to fuck; I have many vivid memories of the sensations of Willow’s mouth in each of those two configurations].
I’m not sure what it is about this particular configuration which I find so hot, but I recognize from myself and from both my fantasies and the actual sexual encounters that I have conjured, that there are several parts of it which are important. One is the timing aspect. The part where the party planner enters to find Willow and me already going at it. There’s something that I would love to understand better about the thrill that I get from that, but the idea of a woman joining a sexual scene fully clothed and from the street, without having participated in any foreplay or preliminaries. That’s not to say that I can’t just have been flirting or playing around with her in a bar. It’s to say that there’s something about her emerging from the street or from the bar, from the hallway really, into the zone of intimacy. Coming from a zone of “the “public” into a zone of “intimacy,” and finding in that zone of intimacy sex already progressing. There’s something about that I find very exciting.
The party planner’s being fully clothed mattered. And in that particular context that I described, where Willow was on my cock and the party planner entered fully clothed, I think it was some time before the party planner lost her clothes. I think I kept her dressed for a while. And certainly in the fantasy in my mind, that’s how I’d like it. I’d like one of the women, at least, and maybe both, to remain dressed. Because to my mind, nudity rarely adds a lot to sex except for functionality. That’s not 100% true because there is value in a striptease. There’s value in clothes being removed. But in those instances, what’s exciting is the removal, not the nudity. And so I think in fact, it might be that removing clothes and then putting on other clothes is hotter than just removing clothes.
So this is all playing out one particular aspect of this fantasy, or maybe one and a half or two particular aspects. The timing aspect. And then there is this other aspect which has to do with the clothing, but it’s not about the clothing. And I’ll say it this way. I think that there is something exciting for me about different levels of sexual intimacy happening at the same time. And maybe different levels of emotional intimacy as well. So in this particular iteration of a fantasy, I want to imagine myself kissing or having my face touched or my hands massaged by a woman who’s probably fully clothed. And I’m imagining that act to be an emotionally intimate act. Whereas, I’d like another woman, thank you very much, to be occupied with my cock. And for her to be fully occupied with my cock. Which is to say, not seeking eye contact, not doing it for my reaction, but doing it for her own pleasure. Using my cock to please her mouth or her hands or her pussy, to simply be gratifying herself as a sexual object, be presenting herself as a sexual object. I could also, in this scenario incidentally, be fucking her face. That would be fine. It’s not that I don’t want to objectify her or that I don’t want to be physically engaging with her. It’s that I want there to be an emotional intimacy being played out at the level of my face and head and a more explicitly sexual intimacy being played out at my cock. And I think what I’m also saying is, and not an emotional intimacy, a sort of explicitly absent emotional intimacy at my cock.
And as I’m saying all of this, I’m thinking, and what if I were fingering the woman whom I was kissing? Or if I were teasing her pussy over her panties or pressing my finger into her clit? And I think that would be excellent and not in any way detract. I’m not 100% certain that it would add from my perspective, although I think I want to think a bit more about that.
There are other aspects of threesomes that I long for. I have a particular threesome in my mind that I’m remembering that was with the Rockette and Isabel. And I’ll link to it, but that threesome, in my mind the hottest part of it was the part that took place in the bar before we went upstairs. And if I recall correctly, the Rockette, blonde, was dressed in white, and Isabel, brunette, was dressed in black. If that’s not how it was, it should have been. But in any event, the hottest thing in my memory was the lead up. That was also true because, as I recall, Isabel got sick. And the actual threesome as threesomes go was more complicated than might have been ideal.
And that points to another feature of me and sex more generally, which I’ll allude to here and flesh out in another post. But that is that for me the best part of sex isn’t the sex. The best part of sex is the part before the sex. It’s the scene setting, the playing, the establishment of receptivity to sex, of willingness for sex. All of that is far more gratifying to me than the actual sex itself. Again, that’s not to say I don’t like the sex, it’s just to say that that’s the part that I really get off on the most, notwithstanding when my orgasm happens to arrive.
So, here are a few other things I like about threesomes. I like the ability for there to be imbalance always being played with. Any parent of a child knows that a playdate with an odd number of children is far less likely to go well than a playdate with an even number of children. Inevitably one of the children feels left out when there’s an odd number. In sex, maybe that’s also true. But there’s another aspect which is hot, which is, as I said, imbalance or asymmetry. It’s that a woman could be sucking my cock while a woman is pouring me a scotch. A different woman. A woman could be kissing me while another woman is masturbating for me. A woman could be riding my cock while another woman is doing a strip tease. And then of course there’s all the simultaneous sex that can happen that’s not so imbalanced. One woman sitting on my face while another sucks my cock or sits on my cock. Two women making out while I go down on one and finger the other. Or fuck the other. That’s a little bit challenging to choreograph, but it’s my fantasy so why not? I think I’m perseverating here a little and I’m going to stop with my fantastical musings. But suffice it to say, in this current moment, when I don’t have a sexual plaything, I’m fantasizing about not having just one, but having two.