Repeating Mistakes – will I ever learn?

This is one from the vault so keep in mind that I was a younger cougar with so much less dating experience under my collar. Like many people new to online dating, I was convinced that I was doing something wrong, I was messing things up or getting myself into bad situations through some invisible, internal flaw. Nope. Shit happens, and the only good thing to take home from it is that it helps you learn and grow.

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 are some of the thoughts I’m entertaining at all hours of the day and night; when I’m washing the dishes, doing housework, zoning out at work, driving the long commute. 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 28-year-old Philip on Plenty of Fish. He was a smooth-faced rarity in that domain of crusty-sunburnt tradie-blokeyness 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 and 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, it didn’t take long for that to dissolve into outright lust and fascination. Of course it was flattering, and even more so considering the 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’s become natural for me to reach out and connect with total strangers online – the hard part is 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 pain 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 tended not to look beyond the current time, and to live very much in the moment.

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 did continue 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.

Internal camera in Philip’s loinslava

We were sitting close together on my couch talking and 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 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 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 and so 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, because my ‘dating age’ is actually 8 years younger than my actual age.

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 but 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 I should have steered the topic away. I dodged specifics and told him that it was around a dozen and in truth, I couldn’t remember how many because the number was not important to me. They were each individuals and each filled me with the promise of satisfaction and some sort of future beyond that.

And 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. In this case 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 and 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 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 doorway in my Chinese silk dressing gown and waved him goodbye.

After a record in non-communication of two days, I texted him and he explained 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 would 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. Usually a mistake, I found our awkward texting false and unsatisfying. I stopped responding and he disappeared, again.


A Dating in Midlife Adventure

One man’s search for sex on tap, a full belly and a roof over his head

Within the first half hour in his company, 50-year-old Simon told me that he’s looking for a good cook and a regular sexual partner to meet his daily desires – he prefers oral over penetration because the old fella doesn’t work so well anymore, and he’s got a bad back. He’d like a blowjob every day and if he likes the smell of me, he’s happy to pleasure me in return.

Later, on my drive home, I decided that despite his generous offers of near-constant orgasms (assuming of course that I met his olfactory standards), the guy was living in fantasy land. He also lived too far away from me and had an unreliable availability pattern due to working on demand in a low-paid service industry.

In short, Simon was a bad match despite our chemistry, which undeniably did exist. The way he’d brushed my nipples and when I allowed him to briefly explore my naked breast, his fingers knew exactly what to do to make me gasp.

I should have listened to my instinct when we first connected a couple of weeks ago on Plenty of Fish.

I’m making a strong effort to meet and give chances to men in my age bracket, or even a little older. This cougar’s trying new tricks because the young ones are problematic, to put it mildly.

Simon’s profile photos showed an attractive mid-life guy in good shape, with a winsome, hippy-flavoured user name – plus 16-year-old photos of his heyday living on an African commune wearing sun-bleached dreadlocks and just a pair of skimpy shorts over his all-over bronzed tan. (What was that about? Imagine if I posted photos of the same vintage! And why would I?) We’d shared an opening line each on POF and then he disappeared for a week.

Our next messaged conversations were disconnected and jarring. After his brusque request for more photos (I already had six uploaded), I deleted his thread and moved on to other conversations.

Simon was persistent and returned to our conversation, asking why I had disappeared. I told him frankly that in my experience if a guy immediately asks for more photos, what he really means is ‘show me your tits’ or ‘give me a nude’. He backpedaled and so I decided to give him a decent go at convincing me.

We moved our messaging to kik and the awkwardness continued until I confronted him about his bull-at-a-gate attitude. He seemed to expect that he could achieve the delicious highs of smitten new love immediately, with little or no effort or time to get to know the other person and their authentic self.

“Are you new to this?” I asked. “You need to allow time to get to know someone – you can’t just have instant intimacy on a plate and happy ever after,” I said, feeling as if I was explaining the obvious to a kindergarten child.

“I know that, hun,” he said. “I’m not angry with you I’m just sick of this online dating shit.”

Fair enough, I thought. It is sometimes crappy and often frustrating, but that’s a naïve attitude to begin with. We managed to develop a tentative rapport after that, and seemed to be on the same page sexually, so I suggested we meet up for a coffee on my day off – a couple of days away.

The frost was still thick in the winter air when we met at the café and I noticed him watching me from his driver’s seat as I climbed out of my car. He looked like his pictures, which was a pleasant surprise, and as he hugged and kissed me on the lips I felt his enthusiasm.

I don’t actually like to be kissed on the mouth on first greeting – I find that presumptuous and invasive, but I warmly greeted him anyway, and we ordered our drinks. I insisted on paying for my coffee. He baulked, but I already knew he earned a lot less than I do, plus I didn’t want to feel obligated in any way.

As we nursed our coffees and talked, sitting on a bench under a historic, winter-bare oak tree, the feeble sun warmed our bones. I kept the conversation bubbling smoothly by focusing my questions on him and his rather interesting life.

As a citizen of three countries, he’d only lived in Australia for the past 14 years and his accent was a hybrid proof of his past. His manner was blunt and strangely detached, incongruous for one who claimed in his POF profile that keeping the honeymoon period alive was his greatest desire.

He felt no compunction about moving closer on the bench seat to fondle my breasts, and given our sexually charged texted conversation and my desire to build a regular sexual relationship (if nothing else, though that’s not my ideal), I didn’t mind too much. But I certainly noted that behaviour and his subtle sense of entitlement.

He hadn’t mentioned that he was father to a five-year-old until now, and he said that it seemed to repel women of his age, whose children were a lot older or who didn’t want the burden of a man who came with that sort of high-maintenance baggage. Next I discovered that he was a ‘Sunday Dad’ and his one day with said daughter fell on my one kid-free day.

And then he dropped the bombshell that fell with a muffled feathery weight. I’d been saying that a man’s kids were no concern of mine as I wasn’t looking for anyone to live in my pocket, or indeed to cohabit. Two decades of that were more than enough!

“Well actually,” he said, “I’m looking for a partner to move in with. Not right away, of course.”

The text comment about my cooking abilities floated into my thoughts, which I’d read as a bit of a joke. It now appeared that he was serious. He lived in shared accommodation, had a casual and unreliable job, and was desperately horny!

In hindsight I can see that from then on that morning, his attitude subtly changed. He stopped trying to nestle against me and the conversation remained firmly focused on him. During the entire hour and a half together he asked me one question – what I did for work.

While we strolled in the fresh air around the nearby park, he walked several steps ahead of me and didn’t turn to speak – commenting to the air instead. He pulled me into an awkward embrace on the pathway and cupped my breasts while kissing me again, but he didn’t linger, which seemed odd at the time – as if he couldn’t be bothered actually trying for authentic intimacy.

As we sat on a park bench in the sunshine, we kissed again and his hands wandered, but he barely listened to me speak as I responded to his question about my last serious relationship.

“Oh and I can’t do lots of positions,” he announced. “I’ve got a bad back and the little guy doesn’t behave himself sometimes. I really like to be sucked. I’d love you to suck me right now.”

I laughed at his boorish enthusiasm, while reeling at his gall. There was a peculiar feeling of harmony (sexual chemistry) juxtaposed with a complete disconnect around values, beliefs and what we were each looking for. “All good things come to those who wait,” I quipped. “Just be patient.”

At this stage I was still stupidly hopeful that we could become regular lovers, so we talked schedules and logistics, my mind on practicalities rather than the bigger issue of whether we were indeed compatible beyond the bedroom.

I was also quietly absorbing his revelations that his tackle wasn’t fully functional – something I am coming to see is extremely common in men over 45.

“While many women in their 50s and up say they feel more sexually liberated than they did in their 20s — finally released from the worry of getting pregnant, and more comfortable with their bodies — they are frequently tumbling into bed with men who suffer from erectile dysfunction. ‘I hear this from a lot of my girlfriends, and it’s depressing,’ writer Kerri Sackville said. ‘Finally, [they think] “I’m going to have great sex”, and it’s not working, and there’s nothing you can do about it.’” (Heart Ailments and Erectile Dysfunction: Life on the Dating Scene for Women Over 40, ABC, 4 October 2017)

As if this picture wasn’t depressing enough for those of us who like and are sexually attracted to men, comes the research findings that men who have regular sex over aged 50 may just be increasing their risks of heart attack.

“Because older men have more difficulties reaching orgasm for medical or emotional reasons than do their younger counterparts, they may exert themselves to a greater degree of exhaustion and create more stress on their cardiovascular system in order to achieve climax,” said Professor Hui Liu in the Journal of Health and Social Behaviour.

Simon kissed me goodbye and fondly patted my bum. I couldn’t help but feel it was an insincere gesture and sure enough, he messaged me a day later.

As I predicted, he’d decided that he was going to focus his attentions on meeting the woman who ticked his required boxes (sex, food, shelter). Sigh. It’s so boring when my intuition is right all the time. Just occasionally I’d like to be surprised on a date by someone who is actually great!

Onwards and ‘upwards’ for me – even if not for the men I’m meeting these days!