I am a 51 yo, mwm. I had some teen experiences, too. Mostly oral, but I received anal a couple of times and thought it was great. When I got married, I put down the active play, but I still used the memories of it as masturbation material. I'm sure you know what I mean....I'll bet you do too!
About 5 years ago, I met a (divorced) guy via our mutual interests in clock (and other mechanicals) repair. Over time we discussed a lot of things. Sex became one of them. At some point we brought up our premarital MM experiences. Like me, he had not done anything with another guy since his late teen years. It only came up once and was dropped rather quickly.
I started pondering about the possibilities of trying it again. Once I started thinking about it more often, the thinking became more like an urge. I was conflicted on a number of issues one of which is that I'm married and need to keep it that way. I also couldn't decide if my friendship with Joel was strong enough yet to gamble bringing the subject up again.
One evening it all just fell into place. We were working on rebuilding one of his old Conn theater organs when he simply said, "I'm not quite sure how to bring this up so I'll just let it fly and see what you think".
My first thought was that he was afraid to make a comment on how I was re-doing the electronics on the keyboard. I'm a stickler for trying to maintain an original style or method to retain the flavor of originality. He's more of a let's just get it done guy. Boy was I off base!
"I think I might be bi" was what was actually on his mind. I wasn't really ready to hear that because we were knee-deep in the project and it just kind of came out of nowhere. I just told him I didn't hear what he said (it hadn't registered with me yet). He just said to forget it.
I guess it was at that moment it registered with me.
It took me another second or two, but I finally told him that I might be bi, too. He told me that if I ever really wanted to do something about that, he would be open to us getting together.
I can remember the sensation of my heart pounding in my ears as I was processing all of this. I somehow managed to croak out something like "So what should we do about it?"
He said "Why don't I grab a porno from upstairs. We can watch it and jerk off or something." I said that maybe we could try that. He didn't say anything more, he just went upstairs.
I figured I ought to at least wash my hands. They were kind if grungy from the crud that had accumulated on the keyboard. I went into the bathroom to clean up when I heard his shower running upstairs. It occurred to me that this might get "serious" so instead of just washing my hands I stripped off and stepped into the shower stall. Not knowing how far this was actually going to go, I figured I should at least get the ol' "undercarriage" soapy and clean.
When I turned off the shower, I could hear him kind of knocking around a bit in his den area just outside the bathroom. I wasn't sure if I should get dressed and go out, wrap a towel around myself or just walk out naked. I cracked open the door and peeked out to see him in his bathrobe fooling with the DVD and the TV. I opted for the towel.
I walked out wearing just that towel around my waist. He looked at me and pointed to a bath size towel he'd brought down for me. "Why don't you wrap that around yourself, too so you don't get chilled", he said. I took him up on the offer.