Hopefully that title got your attention!

The various posts on this blog pertaining to the idea of older-younger gay couplings are the most popular. I haven’t written one in a while, so I thought I’d talk about one of my own experiences — with more to come in subsequent posts.

First, let’s call him Josh. This is how we met.

I’ve had profiles on two websites – silverdaddies.com and daddyhunt.com, off and on, for quite awhile (though not currently as of this writing, 11/27/18) and generally think they’re not that effective – the main reason being their niche audience and international reach. In other words, yes, there are lots of gay men who would like someone older or younger to be with when you take it on a macro level, say countrywide or worldwide, but maybe not so many in any particular locality (big cities are always, always better though).

That said, the quality of the men I’ve met on both those sites has been spectacular, if compatible partners have been few and far between. When it worked, it was fireworks. The reason for this? From my point of view as the older man, it’s because the younger men on these two sites are sincere about their desires to be with someone older – it’s the main reason for being there. It’s not just some added aspect of a potential date, like it might be (the age factor) on hook-up sites like Scruff or even Grindr (which skews younger anyway). So – with Josh, I think it was silverdaddies.com.

So, again, on how we met: I was searching the site for younger guys in my area who wanted to meet older guys. Josh had created a profile saying he was very attracted to men 20 – 30 years older than he was and wanted to meet someone for an experience, to see what that was like. I believe he was 24 or 25 at the time. I was in my mid-50s (this happened several years ago).

He included a photo and of course, he was adorable, as the majority of 24-25 year olds likely are. Handsome, dark hair, olive skin, solid. I wrote back, saying I enjoyed being with younger guys and could provide that “experience” should he so desire it from me.

After the usual back-and-forth messages via email, we agreed to meet for coffee. I don’t like inviting strangers over nor do I like showing up at a stranger’s house sight unseen (in Josh’s case, I believe he was living with his mother at the time) because it’s not safe or pleasant to do that. I realize, especially with the growth of the apps, that guys do this all the time now but I still  haven’t been able to get my head around it. Wrong generation I guess. Thus: Starbucks, or coffee chain of your choice, perfect for this kind of encounter.

Bonus points to my heart: Josh showed up on time. We got our coffees and I suggested a walk around the San Fernando Valley neighborhood we were in, as this particular coffee joint didn’t lend itself to private conversation.

He told me his story, or part of it: He was bisexual, pretty much inexperienced with guys, had what he called a “compulsion” for older men (his words: “older middle-aged men”) every once in a while that was this desire he could not explain. I told him that from where I sit it’s pretty common, or at least I’d heard this quite often from other guys his age. We didn’t have a long meeting – I just told him I thought he was quite attractive and I’d be able to provide this “older man experience” he was looking for and he should think about it. And we could make a date, if he wanted.
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Probably the next day I got a message from him saying that indeed he did want to make that date. It would be at my house, and he agreed to the day and time – a weeknight, early evening.

I was nervous, of course. Josh showed up on time, came in and sat next to me on the couch. I asked him if I could touch him (consent!) and he said yes. Before I knew it we were kissing, and he took my hand and put it over his hardened cock (still in his pants) telling me that “it got hard as soon as I got out of the car.”

Yay. We ended up in my bed, naked. He had some tattoos, which I wanted to look at and know the stories behind, but he told me: “I don’t like to talk about my tattoos.” Alrighty then.

I gave Josh the best blowjob I could for that day and time (in other words, stellar). I don’t remember if he returned the favor, almost certainly not to completion as this is way more complicated with someone who has had prostate surgery and has no cum (ahem, yours truly).

Whatever, delightful, and after the sex part, pillow talk. What one older guy and younger guy have to talk about — jobs, living situations, aspirations, that sort of thing. I felt that he tried to project a self-assurance that was not completely formed, if that makes any sense. I wanted to say “just be yourself, it is enough” but didn’t, as I thought it might be too intimate for that kind of moment – and I wanted him to come back again.

He did. Josh and I met several times that year, he wanting my ass more than anything which I finally did feel like giving up to him one night. He looked down at me while he was fucking me and said, apropos of nothing, “you’re going to sleep very well tonight.” He was right. I did.

I suspect that eventually, he got tired of my insistence that we make dates, that I wasn’t too fond of spontaneity, especially at my age and extra-especially for bottoming. There being the huge difference in our ages: I just didn’t have the same libido Josh did. Eventually, he met another older guy at a sex club (who he told me about) and said he really was only interested in this other guy. By the way, he also was able to drop the bisexual label by then and thought of himself as gay.

We’ve lost touch. He was beautiful and he was sweet, and I loved how he made me feel. I’m glad I was able to deliver on that “older man experience” for him. I would have preferred it lasted a bit longer, but it was what it was.