First ‘older’ guy

First ‘older’ guy

I’ve always had a thing for older guys, ever since I can remember. I’m not just talking you’re George Clooney’s, it’s not just about looks; it’s an age thing. Ever since I can remember I’ve been in love with older film stars and men I’ve known. At 19 I was obsessed with my boss who was touching 50, he was not attractive, but he was a cockney geezer who wore a suit, a proper joker and quite a flirt.

Of course then, when I joined Tinder, I was obviously going to have my age limit set pretty high as this was my chance to engage in a little older man action and see if they were as exciting as I thought.

I made a date with a 43 year old, who was not exactly touching retirement, but was 15 years my senior. He was convinced I was a catfish, so I had to send him a photo of me touching my nose, cute I thought. It was purely a sex date, but as he was still unsure I was who I said I was, we met in a pub first for a drink. We got on so went back to his place.

He made me a drink and was clearly nervous so I went over and kissed him. I think this was probably already a sign it wasn’t going to live up to my expectations, as it’s the confident older guys I like, so the fact I made the first move wasn’t ideal.

I was wearing a dress and stockings, so I hoisted my dress up, sat on top of a squishy armchair and pulled my knickers to the side. He went down on me; it was incredible. I ended up lying with my back arched over the chair and my head completely upside down. Sadly, that’s kind of where the magic ended for me.

Pre date selfie

We went into his bedroom and continued canoodling. It was at this point that I could see his face (previously hanging upside down on a chair I’d been oblivious to it). His mouth was open like an excited puppy… I shouldn’t be cruel, but it was entirely off putting. I’m a person, not a prize he’d won, and I didn’t need to be gawped at as such, as though he couldn’t believe he was having sex with me.

It wasn’t just this though. He fumbled putting the condom on (he’d been annoyed he even had to wear one, this always kills my lady boner a tad when you have to argue pre sex). When I said fumbled, I mean it took forever. I was entertaining myself while he tried to squeeze his now slightly flaccid peen into the rubber, and this was much more exciting that what was to come….

He never fully recovered from the condom debacle. Whether he just wasn’t used to them (seeing as he clearly never wore them), his dick was just not up for it. Though it didn’t stop him from trying. Now, I’m all for a trier, but do men not realise that unless you’re pretty damn hard, it ain’t going in? Or if it does, it’s coming straight back out. Plus, it does not feel good. He attempted the doggy position for a little while; I let him work it for a bit to see if it got the blood pumping. It did for a brief minute or two, but I was well and truly over it at this point. He was also huffing and puffing like he’d run 1500m. He collapsed on the bed and suggested going for a smoke. To him this was a joint.

We stood in his shed, while he rolled a massive joint and I had a cigarette. I was fucking freezing with just a jacket on over my stockings (I think it was November). This was not what I had imagined. He was essentially an overgrown teen, with the sex to match.

I decided to leave. I didn’t want a repeat attempt, even though he seemed excited about what was to come (which I suspect chance would have been a fine thing for either of us).

I haven’t stopped flirting with men well into their fifties, I think I just need to choose more wisely.

Leave a comment

  1. August 6, 2016 / 8:28 pm

    Disappointing! My experience with age ranges is mixed. I do expect older to be ‘better’ though. Surely sex is something we should all be learning and growing with time?

    • August 6, 2016 / 8:30 pm

      Totally. Since been with older and was vastly better. I think it’s the confidence some older men have to I like. So I need to stick to that and not just the number!

      • August 6, 2016 / 8:35 pm

        Confidence is so sexy. Or erotic. Or mysterious. Or all of those. I owe you an email too – soon!

  2. August 7, 2016 / 4:30 pm

    I’ve learned the hard way that just because they’re older doesn’t mean they’re any better or more experienced. Such a disappointment! I have my own older man story to tell, and it’s not much better. lol

    • August 7, 2016 / 6:13 pm

      Fortunately I’ve had better since!

    • October 19, 2016 / 7:03 pm

      I don’t think it’s all men of that age by any means. Though I’m sure it gets more challenging or they wouldn’t have invented a pill to overcome the problem. But yea, it was a bit.

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