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.

What Is It With Guys Over 39?

Is that the magic age when women of their own era become invisible or inherently undesirable because we might show a few lines, or signs of childbirth, or maybe because we might be wise to the mid-life male and their foibles and flaws?

Dating statistics in the western world consistently bear out the trend for older men to prefer women a decade or two younger, whereas women (apparently – not me) prefer men in their own age group when dating.

What is not clear from the data is what women were seeking when they ticked that box. Perhaps it was long-term compatibility or companionship rather than excitement, passion and to revive their forgotten sexual capacity.

After all, if a woman is dating again in her forties it’s highly likely that she endured a long period of monogamy during which (again, if the data can be believed) she probably didn’t often get her needs met. Combined with the questionable state of sexual reciprocity in marriage, if the relationship was suffering the agonising slow decline, the chances are that sex was off the agenda anyway.

However, the point I am making here is that – for whatever reason and on average – older men do not seek out their female counterparts in the online dating world.

This is pretty depressing for a woman in midlife, who holds out hope for a mutual and satisfying partnership at some stage during this second half of life. The fact that I can and do attract the young things without even trying is beside the point, because the basic maths shows that a 10 or 20 year age difference is just not sustainable. That was a major factor for me when I chose to end a two-year intimate relationship with my then 27-year-old lover.

Let me illustrate this point by sharing my experiences and perceptions across three dates from this weekend.

After a five-month absence from dating, chatting, texting, swiping and putting my profile out there, I dipped my toe back into the (cess)pool that is online dating. Oh so many bites; I narrowed them down to a dozen and arranged dates with three, based on random selection and even more random timing. There was precious little analysis and it was very quick, because I rarely know how my free time might pan out and when I might be able to claw a couple of hours away from my 24/7 teens.

I chose two guys of roughly my vintage plus a latecomer who burst onto the scene and wowed me with his erotic storytelling and our instant connection via kik messaging.

The 50-year-olds were unremarkable and if I squinted and blurred my vision I could imagine them perhaps being attractive to my tastes.

I withheld judgement, prayed for the best and arranged to see one for a couple of hours on a Friday evening, and the other for the Sunday early afternoon.

I’d been chatting to Mr Sunday afternoon all week and thus far found conversation yawn-worthy and unremarkable. Mr Friday night, on the other hand, surprised me with his eager texting and I propositioned him for the date, knowing all too well that meeting as soon as possible was best. He was very keen and reliable and we met the next night at a local upmarket hotel.

I was standing at the bar when he sidled over to me and said a mild hello. He may have kissed my cheek. We made polite conversation while ordering drinks (we paid separately) and then found a booth in the quiet lounge room of the hotel. Conversation was easy and smooth and I didn’t have to work too hard – one benefit with dating older men is that they usually know better than the young ones how to maintain the conversational flow.

Topics were pretty tame and he sat miles away across the table, with no attempt to move closer to me or initiate any sort of physical contact. We talked casually for almost two hours, covering topics centred around him and his life, although he paid lip service to me a few times. It was pleasant but as I surreptitiously studied him I couldn’t imagine having sex with him, or that he’d ever be in the grip of passion or emotion. He had thin lips and that’s an instant turn off for me.

I suggested that it was time to leave and we meandered out to our cars. As we said goodbye I felt a surge of unexpected warmth and the next thing I knew, we were kissing. I don’t think I initiated it, but I didn’t recoil because he was actually a pretty decent kisser. In my mind I thought I’d give him a go and see whether he might have potential in bed, seeing as how that was the point of our meeting – to find a lover/FWB/FB (whatever term you prefer).

It was quite a long kiss and it did involve tongues. It wasn’t unpleasant but nor did it trigger any desire to go further, and certainly not to touch him elsewhere. Fortunately he was retrained and didn’t grope my breasts or arse, but he did steer me towards my car and kissed me again in relative privacy. We said goodbye a few minutes later and as I drove home I thought I’d just wait and see what happened next.

We texted a little later that night. “It’s funny what happened when I kissed you,” he messaged. “Didn’t you notice my erection?” Actually I hadn’t and it seemed sort of crass to mention it. Oops, I’m showing my prejudices because I just can’t seem to get excited by lukewarm old farts who consider lawn bowls a suitable topic of conversation on a date.

We had a bit of back and forth banter, and for some reason I agreed to send him a boobiepic (full nipples and all) since he asked. In hindsight, he didn’t so much as ask as demand, which should have been a warning. I pondered and sent him my best, guaranteed-to-produce-oohs-and-ahs full frontal shot.

Now the ex-young lover had a breast fetish so I have quite a few of these in my collection, but even if I do say so myself, this shot is pretty amazing. I am honored to have such boobs, and I really have a surgeon to thank for it since I had a breast reduction operation seven years ago. However, I don’t usually reveal that! So you’ll understand my disappointment when Mr Friday night barely hesitated before texting, “good – very good.”

Fuck you, I felt like saying. Where’s the moans and exclamations and all the hoohar – or is it only the young ones who know how to appreciate a lady’s assets?! It’s not like I didn’t say all the right things when he showed me his saggy man-boobs and graying chest hair.

I had to work late (the joys of freelancing – no, I mean it!) and so at about midnight I stopped in at the site we met to see how my message box was coping with the onslaught. I was still fresh meat and I’d already figured out that real women were in the minority – hence the bulging inbox and multiple propositions. I spent a short time moving some guys over to kik and deleting others, then I went to bed thinking nothing of it.

The next morning, while lounging in bed making up for my late night’s work, I checked into the site again and found a message from Mr Friday evening date. “I saw you were on here tonight,” he said. I casually replied that I had been, and was that a problem?

To be honest, I haven’t logged on to the site since then (the reasons why will soon become clear) but on our kik account my message remained unread for two whole days.* I haven’t heard from Mr Friday night since so I guess he did object to me logging onto the site! We hadn’t even arranged a second date, discussed anything personal and already he wants to control me?! Phew, lucky escape!

Onto second date for the weekend, Mr Sunday afternoon. Also about 50, he was a different type of guy – workaholic, self-obsessed, a nervous babbler and someone so out of touch with his emotions I couldn’t even imagine being in a bedroom with him, let alone having actual sex. We had gelati and coffee (he paid, though somewhat reluctantly, but I let him go through with the offer) and over almost two hours, in his mildly high-pitched voice, he talked incessantly about himself, his hobbies, his children, his ex-wife, his property developments, his study – including his forthcoming assignments – and his love of classic cars and motorbikes.

I was friendly enough because I had a get-away plan and I soon calculated that date #3 held the most potential (young hottie).

Boy was I correct and I extricated myself from Mr Sunday afternoon as soon as possible. So utterly unsexual was he that he couldn’t even manage a peck on the cheek and we hugged instead.

I drove the five minutes to my third date for the weekend, Mr Mid-30s Hottie, who’d been texting me while he waited three hours for me to arrive at our destination. He’d been on a cycling event and rather than drive all the way home, he decided to wait for when I’d be free at 3pm. Sweet – and keen!

“Why don’t you meet me at my car so I can give you a proper welcome kiss?” he messaged on kik just as I was at the traffic lights. I couldn’t figure out where he was parked, so we met at my car instead – true to his word, he grinned and complimented my appearance and then embraced me in a passionate kiss. Now that’s how to make a good impression – especially with a sex-starved cougar who’s had to endure two boring old farts for more than four hours of blathering!

And he was drop-dead gorgeous, did I mention that?!

At least 6ft5, fit and lean, black plastic glasses (just like the pic!) and a nerdy shyboy appeal that hits the right spot for me every time! (I have an internal warning – but he doesn’t sound the alarms because, when it comes to sex, he is voracious and completely self-assured.) We giggled, held hands (while I felt up his arse and he laughed) and walked to the café.

As requested, I was wearing a revealing top and as he sat opposite me I could feel his eyes drinking me in. We made pleasant conversation (yes, it was harder work that the older guys because Mr Mid-30s Hottie is socially awkward,) covering a lot of topics. About an hour later he suggested we should go out to the car. I agreed and we walked hand in hand, with some more arse fondling, to my front seat.

It was broad daylight, sadly, and as neither of us are into dogging (having sex in public – it’s a thing!), we kept it fairly tame though he was very keen to escalate, but gentleman enough not to push it. However, two things were immediately clear – firstly, I really liked him and found him deliciously attractive, and secondly, he found me sexy, hot, desirable and worthy of a second date!

He has this irresistible combination of self-doubt, awkwardness and shyness – but combined with a sexual confidence and the body of a god! And he’s a fabulous kisser – I definitely wanted more of that but was finding the whole kissing in the front seat of a car thing uncomfortable, and there were too many people milling about outside.

So here are my thoughts on the whole age thing – the difference between guys and girls as we age.

I think Lauren is spot on when she says that men tend to get old quickly and set in their ways. They are also less likely to look after themselves and stay attractive. (Blunt I know, but that’s just a comment about their packaging – here’s what’s really important).

On the inside, however, is where the real difference lies – women in their second phase are often highly sexual, passionate and excited to be alive. Men, on the other hand, are often withered, bitter and cynical.

Take Mr Friday and my tits – he may not have seen better in his life (unless they were on a porn star) and yet he could barely raise a compliment and then ghosted me because he was hurt/angry/jealous, [delete whatever is not applicable] because I checked into the site where we both met, after I met him! And let’s not forget that HE checked into the site too!

I have found men my own age to be highly critical of a woman’s body – even sporting their own pot bellies, double chins and craggy lines, they expect youthful perfection in their potential partner. Men of my generation also seem unable to flirt or playfully engage on a level that is mischievous or ambiguous.

I hear this often from other women, and I’m not sure why or whether it’s universal. I guess I should qualify that statement by clarifying that I’m talking here about men on dating sites, or single men looking for something (sex, a partner, whatever).

Most young guys assume that, when you say you like younger men, that it’s all about the sex – that they’re obviously better, more lustful and with greater stamina because they’re young.

I haven’t found that to be the case, although Christine Feminist probably disagrees. She’s had some amazing sexual experiences with young guys, but sadly most of mine have been duds. Being a porn-fucked Millennial is really common! The symptoms are obvious when you’ve been in a long-term relationship and you know how normal men function. I’ll write about it another time. So for whatever reason (region-based, age-based, my bad luck or bad timing), most of the 30-plus sexual experiences I’ve shared with guys under 35 have been abysmal. I’ll be sharing those stories in future so stay tuned!

The important point here, however, is that it’s not the sex that makes younger guys so appealing – it’s the attitude! It’s the fun and the flirting! It’s the passion, the feels! It may not last – but it lights my fire that’s for sure.

As for Mr Mid-30s Hottie, he and I have barely stopped texting erotic tales, flirtatious and rambunctious desires and madly arranging our first all-day date coming up in two days! I can barely wait and the best part is that neither can he.

Time will tell whether he is as amazing in bed as he seems, but thank the goddess I don’t have to wait much longer to find out. Watch this space!


* I checked onto the site a week later and all evidence of Mr Friday night was removed! My guess is that, in a sulk, he packed up and left!