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.

Performance Issues

The Lily Allen song all about her ex who couldn’t please her sexually (or was just too incompetent or lazy to try) floats around my head as I look back on my first unsuccessful, fully-naked sexual encounter.

Maybe I’m lucky to have grown to middle adulthood (that sounds so much better than middle age), never having experienced truly appalling sex. I’ve certainly been lucky in that regard, but nothing could have prepared me for this Bad Sex Experience.

For starters, when a man kisses like he’s in love with you and it goes on and on and actually – though you adore kissing almost more than food – you’re the one who pulls away, that says something about both his stamina and his passion for you.

Well I thought so anyway.

We’d chatted on OK Cupid for only a day before we agreed to be spontaneous and meet the next day, since we’d both be in the city, me for work and him for uni.

Rocco had returned to study his passion (jazz music) at the ripe old age of 30, and he seemed to be intelligent and handsome. At our lunch date I found him attractive but mildly exhausting. He was a nervous babbler, someone who talks incessantly to cover up their social unease. Our conversation was fairly intellectual and focused on books we liked and his attraction to music, why he’d all but given up his former career to return to study. I was on autopilot for the whole thing and I don’t think he asked me much, if anything, about myself.

Within half an hour of briefly hugging farewell, I received a text message from Rocco that went something like this:

“I think you’re really attractive and I like you, but I think I’m more interested in passionate sex with you than in a relationship. What do you think?”

I laughed out loud as I read the message while waiting in my car outside my son’s school. I punched in a witty reply that I was certainly up for it, and what did he think about having a kissing date first? This was fast becoming my modus operandi, but I was still in that nervous territory of not quite knowing how to progress beyond conversation and flirting to actual physical contact.

The second date

We agreed to meet in a couple of days’ time, a Sunday, in a quiet but public garden setting. In the meantime he texted me regularly and we worked up quite a rapport and a mounting sexual tension. This was apparent the moment we arrived at the gardens, when he somewhat nervously pulled me into a sensual kiss. It was stirring in all the right ways and it left me wanting more.

Rocco and I wandered around on a bold blue winter’s day, hand-in-hand, arm-in-arm and with regular pit stops to reacquaint our mouths. The daffodils and tulips were blooming and the deciduous trees around us reduced to damp, bare branches through which the sun shone steadily. He found my kitten whimpers sexy and slightly funny (so did I). It was a highly charged day that promised future explosive sex.

We set the date for the following Sunday at my place. In the preceding week we messaged most nights. I knew I wasn’t feeling a strong emotional pull, but that was fine since he’d made his intentions clear. In fact, he’d elaborated quite a lot since and was keen to have a longer-term sexual arrangement if our chemistry was aligned.

The third date

Nothing could have been a better greeting than being pashed instantly and gorgeously the moment I opened my front door, pashed into the house and pashed standing up, his hand on my bum, my waist, my breast.

Nothing could have told me more clearly that he wanted me than him pashing me all the way to the bedroom and us falling backwards in a glory of lust. Finally-to-be-fulfilled-and-satiated lust.

Well, I thought so anyway.

At first it all went splendidly well. The attraction was mutual, the kissing was heavenly and several times I had to stop for air because – as divine as it was – I just wasn’t getting enough oxygen.

The first sign of a problem was when we’d both gently but urgently stripped each other bare. We were wrapped around or on or between each other in a tangle of limbs, warm bodies and tangible expectation.

I hadn’t even had time to think about whether or not he found me attractive, did or didn’t like my curves, boobs, legs etc. It was all on display there on my bed, but he was devouring with me with his hands so I guessed (in some absent part of my thinking brain) that he actually did fancy me, even naked!

Things were looking good and though there’d only been a hint of the promised multiple orgasms, I’d decided that I was well ready for some inside action.

And then Mr Floppy made his appearance.

I found out afterwards that before Mr Floppy asserted his unwelcome presence, Mr Shoot-Too-Soon had come to visit. I hadn’t even noticed.

On and on it went. Though the kissing remained a constant source of pleasure, I was growing increasingly alarmed at not only the lack of attention being paid to my own erogenous zones, but the pattern that was developing.

We did talk about it – we laughed about it too – amid lots of eyeballing each other (he was a starer) and lots of reassurance from me that it didn’t matter.

Truth is, it wouldn’t have mattered if he hadn’t been so selfish. Or as Lily Allen so aptly puts it, “so mean”.

If he’d moved beyond his own failure to perform and onto delivering his oft-stated promise pleasure to me, everything would have been as close to okay as possible when actual penetration isn’t forthcoming.

But no, they were empty promises. The most difficult thing to believe is that someone so proficient at passionate kissing could be so inept at pleasuring a woman, and so unwilling to even try to step outside of his own body and to explore another person’s.

Even when she’s right there, naked, the woman of his admitted fantasy, ready and willing.

So instead of five hours of orgasmic sex we had, at best, an hour of unsuccessful intercourse, an hour of kissing and fondling, and three hours of looking, talking and cuddling. Though it felt like we were intimate, in my reflection the next day, I named it as physical closeness without the emotional content. It was looking but not opening up. It was stroking and fondling without the satisfying moments of completion.

It was confusing, and in hindsight, tinged with sadness because this man – such a disappointment – was also such a beautiful kisser and held great potential. And he was a man too embarrassed to try for a repeat, or to try for anything, because he can’t deliver what I want and need.

Rocco told me several times that it wasn’t me, it was him. He had stuff to work through. He implied that it had never happened before. He told me I looked at bit like his ex. He confessed that he’d come instantly as soon as we started touching.

Ultimately he’d left me unsatisfied and yet when he told me by text message the day afterwards that it was probably best not to see each other again, there was The Sting, the twinge of pain, the racing heart of rejection. He’d left me unfulfilled and confused, ripe for the picking but left hanging, wondering if it really was something I’d done, or hadn’t done, been or hadn’t been.

Rocco joked that too many hours of wanking over my picture had robbed him of the ability to perform with the real thing.

It left me wondering about that human connection, those hours of lying, naked, in bed together and talking – or not talking – or touching. The false alarms, fragile erections that melted into a useless softness. Wondering whether that human connection – in the scheme of things – meant anything at all.

Rocco disappeared from my life for a couple of months, and then we started messaging again, as the mood struck. When he tried, somewhat tentatively, for a second chance I struggled with an answer.

Was it always a bad idea to revisit the past? Was it weak of me to give it another go? He was a genuinely pleasant and intelligent man, but was that enough?

In the end, I decided that he’d had his opportunity and lost it. There really wasn’t anything to be gained by going for Round Two.