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!

28 thoughts on “A Dating in Midlife Adventure

  1. This definitely doesn’t make me want to reconsider meeting men my age or older!
    I think we don’t trust our instincts often enough. We feel obligated to give a benefit of the doubt that we already have signs shouldn’t be given

    Liked by 2 people

    1. I agree absolutely! That is also my problem all over. Now I’m doing what I’ve always done so many times, just with a different age group! It’s partly in my nature to give people a fair go, but I do need to work some more on which people 🙂

      Liked by 1 person

      1. I just ask myself “do I want this?” and I try to be honest with myself if I do or don’t. Easier said than done, but that simple process OFTEN reminds me that I don’t want to even be in touch or meet

        Liked by 1 person

      2. I too would agree with Christine’s comment (about trusting instincts) and your observation about needing to work some more on which people (to meet). More online “due diligence” is the key before wasting time meeting inappropriate “legends in their own mind” type sex gods! 🙂

        Hi, just recently discovered your blog, read all your past archive postings, looking forward to following your further “cougar searching” adventures. Hang in there, lady.

        Liked by 1 person

      3. Thank you – that is a very kind comment. I am muddling on and maintaining positivity, which I do mainly through taking breaks. I am not exactly a cougar, but I use that term to denote mature female sexuality. Hope you enjoy past and future posts!


  2. Eww, he sounds annoying! Yes, our instincts are so rarely wrong… yet sometimes we keep going hey, because we’re a bit bored, or horny, or feeling desperate or charitable? *sighs
    I’m sure a good one is out there honey, you just gotta keep sifting through.
    And yes, the ‘old fella not working well’ is definitely something I came across too, dating men over 50; it must be such a challenge for them; and yet, if it makes them better at pleasuring us… that’s a win 🙂 x

    PS: As soon as I’ve finished blogging about this damn ration challenge [ends today], I will blog and link to your interview of me etc xxx

    Liked by 1 person

  3. He sounds like a narcissistic asshole… only worried about his own wants. What a jerk. I’ve met men like him before.

    On the other hand, I do notice that men who are more physically fit can get it up much better, so being fit is a requirement for me.

    Liked by 1 person

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