Tag Archives: intergeneration gay romance

Real Stories of Older-Younger, Man to Man Sex 1: Josh

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.

Ten Reasons Older Adult Gay Men Like Younger Adult Gay Men

Christopher Isherwood (l) and Don Bachardy in the late ’70s.

For this week, the 10 reasons from the point of view of the older guy in the intergenerational pairing. *

Again, these are reasons I’ve come up with myself from my own experience or anecdotally from things I’ve observed.

So here we go, here are some possible reasons an older guy might seek out a younger adult guy:

He’s adorably beautiful: well, duh. The cynics among you will say that this is reasons 2 through 10, as well. Got to admit there is something about that dewy fresh flesh that springs back when you touch it.
He’s agreeable: from postponing dinner till nine to having a Diet Pepsi when he really prefers a Diet Coke (cause it’s all you’ve got) younger men can be more easy going. There’s that shrug: whatever.
He’s enthusiastic: younger guys will often (if not always) want to do something with a consuming passion! They don’t merely say yes; they’re all in.
He’s GGG (good, giving, game) – this comes from Dan Savage and his “Savage Love” sex advice program — he strives to be good in bed, to be giving to his partner, and game to try out something which may not be #1 on his own list (see enthusiastic, above).

He’s respectful: By the very nature of finding himself with you, he’s respectful of all the gifts an older person can give to an individual and to society; it used to be that everyone was raised to be that way, these days, not so much.
He’s trying to please: I find that this urge to please the older person is almost always part of the dynamic, often unexpected. But I’m not complaining.
He’s teachable/nurturable: Oscar Wilde famously said, “I’m not young enough to know everything.” But all twentysomethings are not that way, and often I’ve found younger men wanting to learn things that life experience has already taught someone older. (I was not this way, however, I was young enough to know absolutely everything! Now I’m trying to unlearn it all.)
He’s usually more interested in the larger cultural landscape: what I mean is that he often will have interests beyond the narrow diversions of his own particular generation. It may come as a keen interest in winemaking, or opera, or deep sea diving.
He’s accommodating: He knows he can’t have everything his own way so is more likely to compromise and enjoy the differences between the generations, and he’s authentically interested in learning about those differences.
Finally, he’s trusting, he’s expecting that level of integrity from you because you’re an older, hopefully wiser, person. In our cynical times, that’s a refreshing quality.

Just for the record, I’ll date someone of any (adult) age. It’s always an individual attraction thing for me, and there’s no specific type I’m looking for. Do you (either younger or older) date out of your own generation?

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Ten Reasons Younger Adult Gay Men Like Older Adult Gay Men

yes, of course I’m kidding.

From the intergenerational dating realms. . . *

It’s no secret among friends and acquaintances that I’ve often dated men younger than me, sometimes, so much younger (20s, 30s) that I could easily be my adult counterpart’s parent.

The usual response I get from gay men my own age to this is positive; they understand the attraction from my point of view, and many have been in similar situations. Female friends can be, well, less understanding, and in my experience, it doesn’t matter if they’re gay or straight women – they often just don’t understand it (but what do you talk about???)

The short answer to that is, of course, we talk about everything. But wait, what about the younger man? It’s easy to see why an older person would be attracted to younger, in fact, our entire society is based on youth worship! But what about the younger guy? What, in heaven’s name, does he see in the older fellow?

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Here’s ten reasons, totally anecdotal, taken from my own life or from what I’ve observed over the years:

Experience: from the bedroom to the boardroom, older guys usually, though not always, have a better sense of what’s going on. And will be happy to share it with someone younger/not in the know.
Decisiveness: After a certain age, a man usually knows what he wants or doesn’t want and isn’t afraid to vocalize that. Maybe it’s because we realize we don’t have all the time in the world and don’t want to waste it being uncertain.
Mature physicality: I’m constantly amazed that there’s so many younger men who are physically interested in a more mature body, whether it be for the hair, the salt & pepper color, a belly, those distinguishing lines in the face — whatever it may be, there are younger guys who specifically look for those traits.
Money: Let’s face it, some kids are gold diggers. Some older people are, too! An older guy is more likely to be more settled, and a mature relationship with finances can be an anchor during those restless days of youth. In my case, I always tell them I’m a sugar-free daddy.
Mentorship: A lot of young men are at a loss in terms of job and educational advice. They’re not getting it from home and they’re not getting it from the culture. Many of them may have run up against a homophobic brick wall and have no idea how to approach their future. Older gay men have already been through this and can provide some guidance and perspective.

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Kinks: OK, back to sex and not only that, but an entire way of looking at things. Lots of younger guys find they like things on a more, um, wild side. Older men are more likely to have worked through whatever issues – homophobic, shame-based, whatever – surround some kinky activities, and again, are happy to share experience and knowledge with someone younger.
Direction: Some young people honestly don’t know what to do and are happier when someone puts some structure into an otherwise scattershot agenda. Contrary to conventional thinking, total freedom is not necessarily always liberating.
Home: An older guy is more likely to have a home that he owns or has rented for a long time, along with some of the creature comforts and sense of place that come with that: patio furniture, TVs that work, matching dishes, more than one set of sheets, etc. Not everybody wants to live like a grad student forever.

History: Older men have the perspective of history from their own lives as well as (most of the time) a knowledge of the gay community and the struggles we’ve gone through from Anita Bryant to AIDS to D.A.D.T. and marriage equality (and a zillion things in-between). This kind of oral history or learned experience is priceless for someone open to learning about it. Finally:
Daddiness: That quality of protecting and being protected, of nurturing and being nurtured, that feeling that everything’s going to be all right as long as he’s around. That’s a powerful bond wherever it occurs — and has less to do with age than the personalities of the individuals involved.

I’m sure there are other reasons I’ve missed. What would you add?