When Something Is Missing

~ Midlife Dating Adventures

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.

52 thoughts on “When Something Is Missing”

  1. Some situations are lived for the moment. This is certainly one of them. I’d be disappointed too if after everything, after not reaching climax myself, having them reach their own and then say it was all about someone else. I feel disappointed for you.

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  2. There’s clearly no disputing the worthwhileness of it all in terms of actual fucking. This is made evident throughout the entire write-up, but truth be told, this guy sounds like a confused slapstick who doesn’t know what he wants. Thinking, let alone, speaking of prior lovers while fucking someone else is just…just….like “why?” why would anyone do that? As men, we have an obligation to appear as simple beings, non-complicated creatures. He sounds complex.

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    1. Thanks. I wouldn’t say complex – that I can deal with. I’d say confused and emotionally inexperienced, I hesitate to say immature because I really like him on several levels. I understand and I accept, but that still leaves me …disappointed.

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    1. Thanks! And also for your email. I will reply. Along with this experience I have been flat out with work this week, most nights until midnight. I’ll take a breather soon and digest all this. IN the meantime, onwards and upwards with 3 dates this week!

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  5. I would like Jad’s view on this.
    Think it would be rather interesting.

    …I should clarify for those who don’t follow. She’s a blogger that’s been featured on this blog in the past, who writes of similar if not the same subject matter.
    Yeah, would be quite interesting. Or maybe that that’s just me…

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    1. Yeah I’m keen to know what she thinks although she has a lot of catching up to do. I would say we are two different approaches to a similar topic, but as you know the focus of my blog is not only the sexuality of mature women but specifically those who like younger men. I am also very much about the socio-political aspects of post-internet dating and what this means from a cultural analysis perspective. On a personal note, I’m looking forward to Jad’s feedback.

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      1. Far better description of the differences and similarities.

        “I am also very much about the socio-political aspects of post-internet dating and what this means from a cultural analysis perspective.”
        This garners a deeper browsing throughout your blog, for me personally.

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    2. Okay here is my view on things in true Jad style!!
      After many years of being responsible for my own orgasms never fucking again!!
      There has been a couple of times since I started my journey that the men I had sex with clearly had no fucking clue how to give a woman an orgasm and interestingly enough they were both the youngest.
      I had no problems with telling them what I liked or if they were messing around in the wrong place or if it was too much too fast.
      I would be interested to hear from a males perspective but from my experience it seems as a man ages he becomes more interested in wanting to please a woman and make her cum versus his own satisfaction.
      Now please tell me more about this thing where a man can only cum from jacking off?
      I had this one guy tell me this but I thought it was because I am forcing him to wear a rubber when he did not want to, he said he cannot cum with a rubber and he would have to jack off to finish, I said okay jack off when we are done then…Turns out he did not need to jack off and he came just fine, a little quick actually but he said that happens VERY rarely with a rubber and I did not know if he was shitting me or something.

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      1. Thanks Jad. Erection or sexual dysfunction is a common side effect of too much porn and wanking, vs the real thing. It has been heavily documented and a lot of people have written about the various negative effects on a man’s performance – not being able to come during ‘real’ sex is one of them, along with not being able to maintain an erection or not being able to get one in the first place! Sadly, this is VERY common amongst guys on dating sites and particularly those under 35. Porn Fucked Millennial is not a description I made up – it is a genuine thing. I take your point about not being responsible for my own orgasm – if I am involved with someone sexually I do expect give and take. Orgasm equality is also a real movement – and it saddens me that we are still fighting for this since the 70s and Shere Hite. I will be writing more on this topic in future so stay tuned!

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      2. *drum roll please*…”After many years of being responsible for my own orgasms never fucking again!!” Superb entrance…

        I can’t and thank god I can’t, speak from the perspective of an older man…late 20s youth forbids me, but the idea of a man wanting to please a woman before his own satisfaction sounds like an issue of wanting something more from a woman than just sex. Something deeper. And if that’s true, emotions truly are a curse where sex is concerned.

        Also, dude’s only being able to cum *without* a rubber? Sweet Mary, Joseph and the Donkey! Damn I hope I never face such issues later on in life.

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      4. I think emotions to come into at times though I have had some brief interludes where clearly the guy was more interested in making me cum than his own satisfaction. Some men really get off on that and the fact that I am multi orgasmic helps!!

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      8. Haha well you know the story. I guess I’m one of those “porn fucked millenials” too. It wouldn’t have been as much of a problem had I not been a 31yo virgin, but years of knowing nothing but my own hand from the time I learned to masturbate wreaked havoc on my first few sexual encounters. I was completely desensitized to any other stimuli. Condoms didn’t help either – couldn’t feel shit. Of course, once I fessed up that I was a virgin that cleared my mental blocks and it wasn’t really a problem anymore… except I still couldn’t cum from a blowjob. She tried once or twice but to no avail, and after that she didn’t bother again.

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      9. Hmmm. Fascinating stuff. I guess if you’re willing to think about the issue and discuss it with your partner you’re already on the way to resolution vs someone who really only wants the end result (ie orgasm) and the stimuli don’t matter, nor does human interaction or emotions. The condom issue is harder to address unless we’re talking trust and monogamy. Not coming from a BJ is manageable as long as someone can from intercourse in my opinion.

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      10. Yeah intercourse wasn’t a problem after that. Still would like to experience a complete BJ someday though. Problem is, I’m afraid I’ve been building that up in my head far too much for far too long that I’m afraid I’ll end up disappointed again.

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      15. Oh wow now I’m shocked! Something like that? ! I would have thought a standard expectation unless overtly discussed. And there is nothing wrong with you maturely discussing your sexual desires. It is normal or if it isn’t, it damn well should be!

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      18. lol well it seems to be standard among WordPress bloggers but I have yet to see it in real life. My ex actually told me she had an oral fixation – which I thought was too good to be true – but I still didn’t see it. I guess she decided it wasn’t worth the effort after she tried and failed to get me off.

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      19. That comes down to communication. I think you can take the WP blogging community as representative of the overall community – to a point. I know America is regarded as generally sexually conservative except for pockets such as the kink community for example, but I know from wide and long experience and discussions that oral sex is regarded as the norm, especially by men. Maybe try dating some more experienced women?

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  6. Great post!
    I love the golf ball image – I want to crack one open now and see inside!
    I love ‘porn-fucked millenial’ as well!
    I think I might’ve taken against this guy for some reason, but I can’t help feeling you deserve better! X

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