Adventures in cougaring

I would like to fall madly in love with someone new. I am increasingly realizing that this will necessitate the person being around my age, or at least like 35 (I’m 45). Even a really mature and awesome young person tends to lack…I dunno. Life experience or cynicism or something. I can’t seem to connect with them anymore on anything past a friend or FWB level.

Buttttt a 23yo local sub placed an ad in one of the FetLife classifieds groups and he really did seem amazing and I thought “hey, maybe let’s just see.”

Or, well. It was a bit more convoluted than that. His ad said that he was looking for someone around his own age and monogamous so I didn’t respond to his ad. I commented on a couple of his pics, though, in a friendly fashion. And apparently I piqued his interest despite being all old and poly n shit so he contacted me. I’m not terribly surprised. A lot of guys end up interested in me despite whatever dealbreakers I have. Hell, I was curious about him despite him being 23. People make exceptions for stuff.

We talked for a bit on FL and then met up in person. I remember mentioning to him at some point that I have a terrible tendency to fall for someone just based on them being compatible with me D/s-wise, when underneath it all our personalities didn’t mesh all that well. I think that’s what made things fizzle with Mine (aside from him continually cancelling on me for work). I said I want to be more careful about that in future. I then completely contradicted myself and ended up making out with him a bit and seeing him a second time even though the only spark to our conversations was coming from talking about kink. The thing is, we talked about kink almost constantly (mostly in the form of him barraging me with questions. Insightful questions about relationships and stuff, I should add. Not wank fodder questions). And when we talked about kinky stuff, there was an illusion of us getting along. If I’d forbidden kink-talk, though, our whole date would have been the most awkward of small talk. Pretty much just long silences interspersed with anecdotes about our cats.

I should probably have just been like “welp, you’re nice but I’m not really feeling it” on that first date. I think one reason I didn’t is that he actually lives in a neighbouring city and had to drive two hours each way for our date and I felt guilty about that. And also, like I said, there was somewhat of an illusion that we were getting along. And there were many things I liked about him.

I did tell him, near the end of that first meet, that I enjoyed hanging out with him but wasn’t sure I was feeling the kind of chemistry I’d want to. He said he wasn’t sure he was, either, and asked if there was enough something to be worth exploring further and see if something developed. I said yeah, I thought there was. And shortly after that he started giving me this super obvious “I want to kiss you” look – but didn’t act on it – and it totally woke up my predator instinct and I sat there grinning at him and not making a move until he went batshit with frustration and asked me to kiss him. I did.

We made out a bit and then he discovered how well I respond when he strokes my skin lightly. He petted my arms and neck until the public park we were sitting in faded away and I was just…floating. I haven’t had someone get so entranced by petting me since that lawyer I briefly dated a year or two ago. I miss that. I need that in my life.

I warned him not to go imprinting on me like a duckling or anything because I’m really pretty sure we’re not cut out for any huge relationship or anything. He said he still wants to find someone his own age for his forever-person – also someone who wants to have kids – but in the meantime he saw no reason to deny himself good experiences. We made out some more and then I said I should get going.

A few days later I invited him over to my place. Not – as I explained to him – because I was guaranteeing play or anything, but because hanging out here is free and there aren’t crowds of people around so it’s just more convenient all around. Secretly though I did figure I’d get naked and have him pet me some more, barring anything happening that wrecked the mood. I’m in such dire need of attention from someone who’s actually into it and not just being perfunctory.

It’s worth noting that in the interim between dates, I didn’t miss this kid at all. When I made our second date I didn’t look forward to it. It was just kind of a “let’s get this over with” thing. But, see, the first time or two that I met The Bunny (including when sexual stuff happened!) I wasn’t sure I was that into him, and I ended up being really attracted to him and into him after a while (though…not in love. Times I’ve fallen in love with someone, I think I felt the stomach butterflies pretty much immediately. So that’s something I need to take note of). Anyway, I wasn’t that attracted to this kid, but there was potential there, and we dovetail almost perfectly kink-wise, and dammit, he is smart and self-aware and articulate and those are all things that usually attract me. So I wanted to give it a shot.

To my surprise, when I came down to meet him and set eyes on him for the second time, he looked cute to me. Cuter than I’d remembered. Which seemed like a good sign. Our conversation was awkward AF, and we didn’t really start feeling somewhat comfortable until we started closing the awkward conversational gaps with snuggling and making out, which seemed like a bad sign. And he seemed to be doing the duckling-imprint thing that I had specifically told him not to do. I told him (by way of a bit don’t-get-too-close-to-me hint) that I know I’m not his forever-person but he’ll damn sure be awesome for someone. He said he may end up with someone else but until then, he wanted to be mine. Normally that kind of talk would turn me on, but the initial burst of “Oh, he’s cute!” had been seriously wavering so his big declaration of (temporary?) devotion just felt like an awkward talk waiting to happen.

I did eventually have him give me full-body pets, and also a foot rub, in hopes that it would spark something. He was excellent at both, and yet my previous tiny flutter of attraction kept fizzling out more and more. I didn’t wanna kick him out directly after having him do pleasurable stuff to me – it would have looked too much like I was using him, I think – but I did really want him out. I softened the departure by moving things from the bedroom to the living room: I made myself a snack (he wasn’t hungry) and we watched a bit of Netflix. As we sat there watching tv with him snuggled all up against me he said “So let me ask you this: how’s the chemistry now?”

He’d recently been running his hands all over my naked body and I was still wearing just a bathrobe and he was leaning his head on my shoulder and nuzzling up to me. I couldn’t bring myself to say “Yeah no it’s not working.” I just couldn’t. I stammered something like “Oh, so far so good…” and he asked if I’d like to see him again and I said probably.

Then I hustled him the fuck out of my apartment as fast as I could politely do so. He sent me a mushy text when he got home saying that he had a wonderful day and he hoped we’d have many more wonderful days together. I responded “sweet dreams!” (it was pretty late by then). In the morning – before he had a chance to send more mushy messages that would make it harder and harder to extricate myself – I texted him that I thought things weren’t working out for me, after all. That it’s nothing he did or anything, just a fluke of chemistry; I gave things a shot but they just didn’t quite click for me. I said that he’s amazing though and if he ever needs a character reference I’m happy to give one.

He took it well; didn’t lash out or anything, said he was disappointed but it happens. He mentioned, in his closing spiel, that he’d felt like he was starting to fall for me. That’s the thing about dating younger: they tend to fall quickly and easily. They also tend to think they’re on the same level as me in terms of maturity/intelligence/life experience, but they’re not. They just can’t see it from their vantage point. So there’s this big imbalance that they can’t comprehend.

It’s frustrating, though, that no matter how brutally honest I try to be, this shit happens. And not just with younger folks. I gave this kid my usual spiel, right upfront, that often I’ll be into someone for a short while and then suddenly I’m not. I told him the age gap would preclude me from having serious feelings for him so don’t get all wrapped up in me. And yet he did (at least when I bowed out he didn’t seem shocked or act like I did some mean bait-and-switch). I gave The Dandy that same spiel, back in the day, about my unfortunate pattern of abruptly losing interest. At the end of our first hookup he still said “so I assume we’ll be seeing each other again?” And sure, The Dandy ended up being one of the relationships that stuck, but that’s kind of a fluke; at the time I wasn’t all that attracted or into him yet.

I try to be so careful with potential partners. I tell them my wants, intentions, and downsides as bluntly as I can. I’m not sure why I bother. People believe what they want to believe.

2 Comments

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2 responses to “Adventures in cougaring

  1. D/s compatibility doesn’t overcome personality differences…and age DOES make a difference! Nice account.

  2. OMG. I can relate to all of this. Yes. Exactly. I go hot and cold easily as well and I’m so done with 20 year olds and yes no matter what you tell them they believe what they want to. Dating in your 40’s is not “not fun”, but it sure is complicated sometimes.

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