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.

When Something Is Missing

Part II of What Is It With Guys Over 39?

Mr Mid-30s Hottie (now renamed The Giant) has come and gone, I think. I am sitting with my ambivalent feelings about this because right now, I’m not quite sure about our experience and what he gave me, apart from his sexual desire and his companionship for a short time.

You know that saying ‘here for a good time not a long time’ – actually I loathe seeing it on dating sites – but in this case it’s kinda apt.

I should have taken more notice when he said to me quite bluntly in my car last week, as we were kissing and flirting, that I’d caught him on the rebound. I asked him why his last relationship had ended and how long ago. It was only six weeks prior and I immediately said, “Oh that’s very recent – are you sure you’re ready to be doing this?”

Turns out he wasn’t. It’s a pity it took four hours of sex with me to realize it, but I guess I can’t complain, although I will, because I do feel sad and let down. This is what my wayward heart is grappling with: it’s not often that I get the tingles and really like a guy, or even that I’m really attracted to someone. The young ones yes, it’s more common of course because they are in their prime and still ripe and juicy. But it’s still pretty rare for me to get the butterflies and all the good warm feelings when I think about someone, chat or flirt with them, and of course spend actual physical time with them.

In the case of The Giant, I already divulged my instant attraction and our slightly awkward café first date conversation (I didn’t mention that he knocked over his coffee and it splashed droplets all down my front, his t-shirt and spilled all over the table). For a while, things only got better after that first two-hour date and frontseat kissing. The sexual tension was high in our messaging and we were both excited and eagerly anticipating our day together later in the week. It was five long sleeps (and lots of flirty messages) until that day arrived, and when I opened my front door to see him standing there, I felt relieved as well as excited.

While I’m grateful that I get any free time at all, it’s difficult having to wait so long between dates due to work, children and to squeeze into each other’s schedules. I’d already discovered that The Giant and I only really had one day a fortnight in common, and that my main day off (Sunday) was the only day he was free to pursue his passion, mountain biking and running. So it was not looking terribly do-able in terms of the diaries aligning, but where there is will, there is a way, and so I didn’t give it much thought.

We kissed passionately on the doorstep. I was barefoot in a cute purple skater dress and cardigan and I’m only 5ft5, which is probably why he seemed so massively tall all of a sudden. I’d been wearing low ankle boots when we’d first met, and this time, as I reached up to kiss him and felt swamped in his embrace, I realized that he must be about 6ft 5. A big guy – and in all respects a big guy! I loved that, especially as I have something of a penchant for tall dudes.

I ushered him straight to the bedroom after some more kissing and while I put my dog outside, he whipped off his clothes, and stood waiting for me, thus depriving me of a favourite activity – that first peeling back of the layers to find the common humanity and vulnerability that we hide under our clothes. Instead, he wanted to strip me and so he gently pushed me backwards onto the bed and lifted my dress off, unhooked the bra and rolled down the leggings and underwear to reveal my naked flesh.

Surprisingly, I didn’t feel self-conscious although we’d had some discussions about his super fit and sleek bod vs my curvy, post-children bod, and my slight anxiety that he might not find me to his taste. He’d reassured me that he loved my curves, and that his last girlfriend was just like me.

Kissing The Giant was pretty amazing; passionate and arousing – even more so because I never seemed to get as much as I wanted before he escalated. In my imagining of this much-anticipated union, I extended the tease and the touch factors and spent some time getting to know his body. In reality, the kissing very soon led to some breast kissing and then he was suddenly between my legs and kissing me there. It was nice, but it wasn’t what I expected, and it seemed too soon.

I wanted a slow lead up to oral sex, lots of kissing and mutual exploration. The stories we’d told each other seemed a million miles away and his promises to ‘make it all about me’ and revel in touching and kissing me all over didn’t seem to manifest in quite the same way. For starters, he penetrated me way too quickly. Now, I love penetration don’t get me wrong, but a lot of fucking early on can actually make me feel very sore and then it’s harder for me to achieve orgasm later. Not impossible, with the right touch – but it became clear to me in the first hour of fucking in every known position, that his texted descriptions of his erotic touch and orgasm-creating abilities were not aligning with my own needs and preferences in the here and now.

It was four hours of amazing sex, that’s true, but there was no happy ending climax for me, so it was more of that frustration of being highly aroused and enjoying the feeling of being fucked every which way, but a sort of blockage since he didn’t exactly know how to give me an orgasm. I found this confusing, given his texted erotic prowess, but as we paused to talk (after his first climax), I discovered that he’s had very few sexual partners and never a relationship that lasted beyond two months.

Yes, that’s TWO MONTHS. We’re talking about a 32-year-old hunk of gorgeousness here (I’d got his age wrong before, so he was a couple of years younger than I thought); someone you’d think would have girls hunting him down. Instead, he described his life as an “open book of awkward encounters and miserable fails”. I told him that it was time to change that version of his story. It seems that something always caused the girl to leave.

He’d grown up in a small town in a remote area several hundred kilometers from a capital city, had never experienced the thrills and heartbreak of finding love and lust in high school. He still found it “hard to talk to girls”. A quiet kid, a small family, someone uncomfortable in the spotlight and unsure what he had to offer or even what he wanted from life. He’d moved to the city for university but then dropped out because he felt that the intellectual side of his architecture course was just going over his head. He’d drifted into the routine of being a bicycle courier, and then stuck with it for a decade. The kind of job that someone might use as a stop-gap really suited him and he’d been satisfied with that until the company changed hands. By chance he’d been offered a job in retail using his knowledge of bikes and fitness. He was happy doing that and had no ambitions for anything else, plus he realized that he wasn’t cut out for further study.

Talking to The Giant as I lay snuggled in his arms, I got the feeling that the inside of him was knotted up like the interior of a golf ball. If you’ve ever prized one open, you’ll know what I mean – the almost intestinal quality of the sticky intermingled threads. I wasn’t sure where the feelings were because he seemed kind of empty, as if there was a vacuum where the rest of us stored our hearts.

At one point he fell asleep with me tucked in his arms and his hand resting on my thigh. While he softly snored in my ear, I dozed and thought about how things had gone so far. Tick for mutual attraction. Tick for that special something I was feeling. Tick for very well endowed and incredible body (that was a bonus, not an essential). But no tick for the promised multiple orgasms! No tick for the promise to take care of me first! No tick for understanding my body!

When he woke up, of course he wanted round two, although I was so sore by then that the final hour before he needed to leave was a tender process in more ways than one. And here’s where I get confused. Sex with The Giant was intimate; it was human and very real. He was affectionate, he loved to kiss me, to look into my eyes and clearly loved fucking me too – but I was again disappointed that he is one of those many guys who can only come from masturbating. Isn’t that telling? A guy who’s never had a proper relationship and can only orgasm from the touch of his own hand? That’s just waving a red flag right in my face and falling into the Porn-Fucked Millennial category. I’ve met way too many of them.

Mr Giant told me later that he wasn’t ready for a relationship, that it was too soon after the demise of the last one (on our first coffee date, he’d blurted the tale of how he’d stupidly not respected her sexual boundaries and she’d not been able to forgive him). As I didn’t want any kind of traditional relationship either, we agreed that we’d like to have sex and snuggles as often as we could.

I said I could only do that if he wasn’t thinking of her while he was fucking me.

He pulled me into a cuddle, kissed me deeply and said, while rubbing noses, “I’m not thinking of her.” He was feeling bad that he hadn’t been able to give me an orgasm or ten – I reassured him that it was totally fine and that he’d been a little too rough very early on, and this was the result. “I don’t believe in faking orgasms,” I said. “No, I wouldn’t want you to do that, because then I won’t learn how to please you,” he said.

We hugged as he got dressed, then again in the hallway before he left. It felt special for me because I like The Giant, though I recognize the flaws and the signs that he’s not right for me. Nevertheless, I offered him unconditional acceptance, no promises, no boundaries and no strings attached. But I could tell that he was troubled, that the tangle of strands inside his golfball heart was writhing and slippery with unease.

Later that night we messaged and he told me he was thinking about our time together. “I lied,” he said. “I was thinking of her. I’m really sorry, I didn’t think it would be this hard to get over her.”

I understood. I said all the right things. I told him to call her, that maybe it wasn’t too late, that maybe if he went out on a limb and struggled free from his feelings of inertia and social awkwardness, that she might give him a second chance. I’m not sure if he will, and I’m not sure what I feel about this episode. I don’t regret it, but I admit that I am disappointed.