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.