Broke the Ice With an Old Friend

I never had any jerkoff experiences with friends when I was younger. Only in retrospect did I realize I missed out on opportunities, but I didn't even know it was a thing that was done, and so never acted upon what I now know were invitations. Oh, what might have been.

Over the last couple of years I've tried to get things going with two different old friends, bringing conversations that, while just shy of expressly suggesting it, opened the door wide for them to walk through if they also had thoughts along those lines. They didn't (which was surprising in one case, because I'm sure he's had bisexual experiences).

But recently a third old friend strode right through that door without blinking an eye, and we finally did what we should have been doing all along. We've known each other since we were 10 years old, and have always been close (even roomed together briefly) but moved apart geographically 20 years ago and only see each other every few years. We decided to have a vacation together to catch up, and rented a cabin in the mountains. No wives or anything, just guy time (at my suggestion). We got to talking about how his wife stopped putting out years ago, and that I'm in the same boat, long since divorced and with no girlfriend. I mentioned that it's a shame that we never had a three-way when we were younger. I said, "Hell, we never even jacked off to porn together." It was a long-planned and rehearsed testing of the waters on my part. It would normally be a risky statement but I knew even if he wasn't into it, he wouldn't think less of me for mentioning the concept. Fortunately, he immediately suggested we watch porn. As we watched, a few feet away from each other on the sectional couch, I was still overly cautious. Unnecessarily. It was quite a while before I even touched myself through my shorts. But when I did, he immediately did the same. I eventually got up to run to my bedroom to change out of my cargo shorts and tight underwear to go commando in some baggy shorts. He said "good idea" and did the same. I still took it too slow. We were both feeling out where the other's boundaries were, and respecting that whatever step we were at the time might be the line. I rubbed myself more blatantly but still over the shorts, and, again, he immediately did the same. I then put my hand in my shorts and he again followed suit. He obviously could tell what I was and wasn't doing but I never saw him look directly at me. I wasn't shy about making repeated and obvious glances at him, though. He had mentioned some ED issues due to medication, and he still just had a semi. I asked if he needed any help. "No, I'm good." Ah, boundary found. He did get hard, though, and we continued jerking inside our shorts, the porn still going. I fully intended to be exposed when ejaculating, though (I didn't need the psychological "oh fuck it" last second push in that regard, but was happy to provide that perception if he needed to justify doing so himself), and when the time came, out came my cock and I blasted all over myself in front of my friend for the first time. Again, he immediately took the same step once he knew there was no social barrier, exposed his dick and came. I made no bones about watching it overtly, and said, "Fuck yeah." He smiled, looked at me and said, "Life is good." I guess we both moaned a bit but I didn't take note of that detail particularly. He got up and got paper towels for us. We had zero embarrassment or shame, and my cock and balls were on full display as he handed some to me. Two nights later we put porn on again. This time, there was no waiting. He took out his dick immediately, so this time I followed HIS lead. Again, if he looked right at me he hid it well. I didn't hide my looking at him but he obviously didn't mind. Both times were were sitting too far apart for any reaching over, if that even was something he'd do. Since we were watching on his laptop on the coffee table in front of him, that was a failed opportunity on my part to use that excuse to scooch closer. We obviously wasted our younger years of friendship in this regard, but it it was fantastic to finally cross that bridge together. A great enhancement of the bond we've always had. He's now getting a divorce, and I'm going to see him in a couple months, so I've no doubt it'll be happening again! I'm curious about ways it could progress, but if it remains just jerking ourselves together that's okay.