Repeating Mistakes – will I ever learn?

In the middle of my first year dating online, I came to an abrupt halt. I’d had a string of appalling sex dates, I’d been messed around, cat-fished and scammed (fortunately I got wise to it and didn’t lose a cent. That story will be in my book.) I’d fallen for someone wholly unsuitable, I’d lurched from one guy to another and eventually, I had to ask myself these questions.

What am I doing wrong? Am I being true to my core values, to myself? Should I be pretending to be someone I am not? Am I making the wrong choices?

These questions on an endless roll of repeat are running through my head at all hours of the day and night; when I’m washing the dishes, doing housework, zoning out at work, driving my long commute. But rarely, it’s keeping me awake at night. I think this is because instinctively, I know the answers.

Memo to me:
No, you are not making the wrong choices. You are making the right choices to learn. This is all about offering up a platter of experiences for you to pick and choose – and experience life. Life doesn’t always go smoothly. Life doesn’t always have an easy answer. Life isn’t predictable. And life doesn’t always give you orgasms. Sometimes life promises up great oral sex and lets you down like a deflating erection.

And that’s a pertinent analogy because right now I need to consider my choices in men, specifically, young men. Men who should know what they’re doing, and should have it all worked out by now – but who obviously don’t, and who clearly, haven’t.

And yet, here I find myself again experiencing the confusion and frustration of yet another unsatisfying sexual experience, yet another guy who promised the world and who did not deliver.

By now you must be thinking I’m a complete loser of a cougar, but bear with me because you might learn something, as I did. (And cougars come in all shapes and patterns!)

I approached Philip on Plenty of Fish. He was a late-twenties, smooth-faced rarity in that domain of crusty-sunburnt tradie-blokeyness (remember, I’m in Australia after all!) and I made sure to tell him so in my light and friendly first message.

I also mentioned that I was outside of his age preference but I wondered if he’d consider chatting to a friendly cougar, since I found him very lovely. He responded enthusiastically! I soon found out that he invested a lot in the idea of me fairly quickly.

The idea of a cougar obviously held some appeal, although I’m not sure why, since beyond that first interaction, age was only mentioned once. We switched to kik after chatting for a while and before a couple of days had passed, we had somehow arrived at faux emotional intimacy. So far, familiar territory.

This time I kept myself under control – I didn’t over-invest too soon, I didn’t reveal too much of my inner life. Although I liked Philip more each day, a part of me knew that it was the thrill of the chase, and the excitement of new intimacy that was propelling me forward.

And gosh-darn, it IS exciting to be talking to a cute and sexy young man at all hours of the day and night, even if the common and recurring theme was how much we fancied each other to bits. It certainly contrasted with the rest of my life, which was predictable in its child- and work-based peaks and troughs.

I didn’t hold back on the compliments and though Philip was initially reserved, before too long, he’d dissolved into outright lust and fascination. Of course it was flattering, and even more so considering the 20-year age difference.

Like so many other experiences, the lead-up to first meeting was sweet and intense.

I tried to catch my imagination and nip it in the bud and on the whole, I did that well. On first impression, I quelled the tendrils of disappointment when I realised that he was shorter than he’d said and that his bad teeth kind of ruined his sexy, full mouth. But I adjusted quickly to the subtle realities of face-to-face, and we talked easily and smoothly considering we were, in truth, two strangers who’d become weirdly connected in a completely unnatural way.

But who’s to say what’s natural anymore? It had become natural for me to reach out and connect with total strangers online – the hard part was translating that to the everyday.

We talked and smiled and found ourselves huddled close together under my umbrella in the warm drizzle. It won’t come as a surprise that I took the initiative and asked him for a kiss. Soon we were kissing passionately and by that time, I’d awakened the beast and realised that he was no shrinking violet or nerdy shy boy.

He was a voracious animal who wanted to have his way then and there in the Botanic Gardens! My body seemed to naturally curve to his and it was the same sweet ache of denial that ran as an undercurrent the whole day.

After several hours of wandering – and wandering hands and mouths – my curfew arrived. I extricated myself from his determined embrace, and while I drove home, I decided that I needed to slow things down and not make the same mistakes I’d made in the past.

Go for the meaningful, genuine relationship (as defined by the two of us).

I put that to him later that night and he wholeheartedly agreed. I hadn’t mentioned polyamory yet because I wasn’t sure of his reaction after such a short period of getting to know each other. I wasn’t chatting to anyone else at that point though, so I was invested in the concept of it working between us in the short term. Everything with younger men was always in the short term. I didn’t want to look beyond the now. I wanted to live in the moment.

Asian food

We met again the following week in the city for lunch on one of my work days. It was a long train ride from the outer sticks for Philip and I appreciated the effort, although when I saw him in my domain, it brought home how unworldly he was. Growing up in the country until just a couple of years before, he’d never even tried Asian food, and that just blew my mind.

A week later, the tension was raised to fever-pitch as we messaged constantly. We shared our thoughts, stories and goals as well as the minutiae of daily life – what we’d eaten for dinner, how his takeaway shop shift had gone, whether my kids were giving me grief.

Because I was wiser and aware of my own predisposition for fantasy-absorption, I continued to restrain myself. But we both discussed wanting something ‘more’ with each other – yes to sex and yes to soon – but it would be the beginning of something deeper.

In the lead-up to the third date, the pressure was cranked. At my house for the first time, he was affectionate and tactile, but clearly nervous. I got the sense very early on that under the surface, Philip was a bubbling, boiling mess and that something in me, maybe something I didn’t even know about, was driving him crazy.

We were cuddling on my couch talking, looking into each other’s eyes when it first happened: a fleeting epileptic seizure.

He’d told me about his ailments – epilepsy and rheumatoid arthritis – both serious health conditions but he’d assured me that he had them under control. As I wasn’t planning marriage with him, I took that in my stride, but after that first quick seizure, I was surprised.

Then there was a second, third, a fourth – all in different locations in my house and each of varying duration but each no longer than a few seconds. During the fifth when we were standing up, kissing, in my bedroom and were just about to move to the bed, he almost broke my teeth with the intensity of the seizure. He was embarrassed but determined to move things forward. I sensed he wouldn’t appreciate me making a fuss.

It was a big turn on that he found me so desirable. He was fascinated by my breasts and when he told me that I definitely did not look my age, I gave a sly inward chuckle (considering I was almost a decade older than he thought I was). Time passed in a blur of kissing and caressing and by the time we had peeled and pushed each other’s clothes off, I almost decided against the condom discussion. My better judgement took over and we agreed that it was necessary.

Our fragmented conversation then turned to why I had a packet of condoms in my top drawer and how many times they’d been used since I’d been single.

I was uncomfortable with this line of questioning and, in hindsight, I should have steered the topic away. I dodged specifics and told him that it was around a dozen at that time. In truth, I couldn’t remember how many because the number was not important to me.

They were all individuals. Each had filled me with the promise of satisfaction and some sort of future beyond that. But every time they’d let me down.

Here I was, poised on the edge of great sex with a well-endowed man who seemed to have no trouble with his erection.

Until the point where he stopped playing with my bits and climbed on top of me.

I have to confess that I adore being penetrated. The first moments are blissful and fulfilling and even if I don’t reach orgasm, penetration-only sex can be amazing. However, the one prerequisite for satisfying penetrative sex is a good strong erection.

Everything was going swimmingly – we were working together, our bodies in harmony – and then, pfffft, nothing. It was all over and he rolled off me, ashamed.

I lay there utterly perplexed. It had lasted less than a few minutes. There didn’t seem to be a climax, just a slow deflation and a sudden end. I was shocked and confused. It had happened to me again! What the almighty fuck?!

There was no clear thought in my head; there was only a racing pulse of blood and a rising lust for satiation. We talked and kissed some more and soon he was ready to give it another go. I switched position, feeling the eye-closing ecstasy of penetration again as I straddled him. Philip rubbed his face between my breasts.

I won’t even describe what happened next – let’s just say a repeat performance – or a distinct lack of. Anti-climax is the word.

After that we talked and kissed some more and I tried to subdue the rising tide of injustice. He called me a randy school-girl and maybe I was. In some ways, I fitted that stereotype but in truth, I was a deeply unsatisfied mature woman who had every right to expect some level of mutual pleasure.

What about all his talk of pleasing me and how much he loved giving pleasure? Another guy who was all talk?

We did discuss it in a roundabout sort of way. Philip indicated that it was not the first time and that every man – if he’s honest – has some degree of performance anxiety. And then told me the story of his previous and only three liaisons since being single for the past two years.

After sex, they had refused to respond to his calls and had cut things dead with him. I didn’t ask whether he’d done the same to them but the implication was there. I couldn’t help myself from thinking, no wonder!

It was time for Philip to leave. Ever since the ‘deflation’ he’d been focused on getting to work on time. I stood in the front doorway in my Chinese silk dressing gown and waved him goodbye.

After a record in non-communication of two days, I texted him. I couldn’t bear being ghosted or ignored. He texted back straight away, explaining that he needed to think things through. After another four days of silence I sent him a longer message that voiced a fraction of my complicated feelings in the most gracious and forgiving way I could manage. He didn’t reply.

I moved onto the next experience, the next guy and the next disappointment. In truth, my hope sprung eternal that I would one day find a man or two who’d be a good fit for me, and be willing to consider me as a sexual equal and not as an object from which they could take their pleasure.

The lack of reciprocity was really starting to get me down, but I was resilient – and still addicted to the online dating game of endless new faces and new possibilities.

About six months later, Philip messaged me to say that he wanted to ‘rekindle’ our spark. Cue eye roll. Can this ever be a good thing?

He’d sorted out his life and wondered if it was too late to apologise. I said I didn’t know whether I was up for anything but I was prepared to be friendly. We chatted for a few days but I found it awkward and false. After only a short time I stopped responding and he disappeared – again.

22 thoughts on “Repeating Mistakes – will I ever learn?

      1. Classic is front page of the Herald Sun this morning and a centre page spread…. I hit the bullseye with the Essendon supplements farce in the first 2 days it happened, and now Nathan Lovett-Murray has followed through

        Liked by 1 person

      2. Major radio calling for royal commission… broke this morning. This is an issue many met me online over in the last 7 years. Call me… Mr Barney Right. Lol

        Liked by 1 person

    1. Thank the goddess for that! You know, I read so many shallow blogs about dating and sex – hardly any mention the orgasm gap or the sexual incompetence of so many men, let alone these low-level stories of crappy experiences. It’s like they go into a vault of silence.

      Liked by 1 person

  1. “The sweet ache of denial… “That made me smile. 🙂

    I don’t know if I could do it, the constant ebb and flow.

    The performance thing was kind if eyeopening. I’m wondering if looking to older women initially gave him the idea it could help him navigate his situation. Hoping she (you) would educate him, or teach him how to prevent it. Do you think he might have thought that if it were to happen with girls in his peer group it was a subconscious/psychological way to prevent pregnancy (never mind the condoms) and when he attemped with someone who had been there done that and wasn’t in that whole biological clock mentality (sorry I’m bring presumptuous) maybe he was testing himself? And when it happened with you, a cougar, he got embarassed?

    Anyway, you have a wonderful way of writing, the flow, the intrigue…it’s all there. I love reading here.

    And finally, I think we all want what you’re looking for. Good luck. 🙂

    Liked by 2 people

    1. Thank you for the multiple compliments here! That is such lovey feedback. To be honest, I think he may have been aware of his feelings about this issue, but he was more likely in denial and hoping it would never happen again. I’m not sure what else I could have done to build his confidence, and by that stage (early on in my dating as an ‘older’ woman stage), I was so over having men do this kind of thing that I didn’t have much genuine sympathy. This is an old story from about 3 years ago. I have a wonderful partner now, who I met on a dating site, and am supremely happy in all regards. I did my time, and I still enjoy telling the stories 😉


    2. Girls in his own domain had probably already worked him out…. I mean worked him out again (kindergarten playing kiss chase chasey was a false start though evidently not a fluke).

      Liked by 1 person

  2. I remember reading this entry in your blog some time back and obviously the message that you were conveying was pretty clear – online relationships can get a tad tricky especially after they result in real life meetups. People often spend quite a bit of time online but often later, for whatever reasons, don’t make the effort to spend sufficient time in “maturing” the relationship in real life. The phrase “Don’t judge a book by its cover” springs to mind.

    Liked by 2 people

    1. Hi Rob. I haven’t published this story before, but there have been many like it – similar outcome if not the same guy. Yes, you are right about those things you observe. I find the whole topic of changing social expectations and how we behave online to be fascinating, and I like to think and read about this subject, so you could say it’s at the core of the blog. Thanks for your comment.


      1. “I haven’t published this story before”

        Being more specific and as a long time reader of your blog, I happened to read this entry back on August 26, 2018. Your words were relevant back then and are still relevant today.

        Liked by 1 person

  3. Wow! You are so confident and adventurous. I love the penetration too! Rex thought he had a real problem with coming so fast, but since we have been regularly making love he is able to last for about 10 minutes, which just PLENTY for me, as I’m usually almost ready anyway and sometimes I come before him! The I say Hurry up! Hurry Up! He loves to think that he’s ok in that regard. Enjoying your posts darling lady,

    Liked by 1 person

    1. Thanks Naomi, that is very sweet of you – although I am still confused by you sharing Rex’s avatar! I am not some super confident ‘cougar’ though – just a pretty normal woman who’s learned a lot in a short time, and at that stage I was determined to have an experience that recognised MY needs too! Sadly, I didn’t find it with him. Next!


      1. Hi Eve! We are confused too! It all started when he decided I needed my own blog and somehow the duffer got everything mixed up. If you know how to sort it he’ll send you the passwords! Honestly, I think he’s too old and I’m demented! I seem to have ‘needs’ all the time these days lol. Its lovely. I’m doing my version of the journey now and it’s fun remembering all my stress and shocks over the last while. It’s on his blog though.
        Love you xxx
        Naomi 😉

        Liked by 1 person

      2. Thanks, I am still behind. I’m back from holidays now so I will catch up! My best advice about WordPress is to use the customer service people – happiness engineers they call themselves! They are REALLY helpful and will get to the bottom of it.


  4. I started drinking when I was 14 and got sober by 24. I find it very hard to relate to other people… especially most other blokes. They honestly expect a woman to do everything for them. Lucky they only have to make out they are alcoholics on the weekend because I wonder how some of them would manage to get a drink if they were. Oh sorry… I guess they are what I call compulsive drivers or driving addicts. Someone at AA actually got violent with me over that one because apparently their disease is more important than someone else’s kid. I just let my car rest in the driveway because I was busy drinking

    Liked by 1 person

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