I love this site and all the great stories.
If you don't count 'playing doctor' games with another boy on my street when I was a youngster, my first and only (but I'm hoping not final) experience jacking with another guy was several years ago, and, wow, the memories still get me hard.
My buddy and I would occasionally send IMs back and forth when we saw one another online. Sometimes, it would be a complete joke like 'Get out of that chat room.' but eventually, we felt comfortable enough to, very tentatively, acknowledge that we liked looking at naked women online, especially if both of our wives were out together and we knew full well the other would be enjoying the freedom to check out the porn.
We later reached the point where we'd wind up on the same site, talking about the specific women we were both enjoying, then would both acknowledge we needed to stop IMing to focus on other matters. Then, after we'd both cum, it was back to normal conversations like nothing had happened.
Flash forward a few months to a day when the wives had a girls'-night-out planned. My friend and I had planned to grab a pizza that night; nothing out of the ordinary. Checking my e-mail, I saw he was online and sent a joking message that if he really needed to jerk off, I could provide better porn later on from one of the movies I had at home. He replied it sounded like a good idea, and I thought nothing more of it at the time, just that we were kidding around.
We met up at the local pizza place, and then I realized he was serious about the porn thing. He asked about it sheepishly, and not wanting to miss an opportunity for fun, said I had a few collections of porn scenes at home we could check out. On the way back, he wanted to stop at a local adult store to pick up one of the girlie magazines because a local woman was featured (she was a bartender at a club he went to occasionally, so he was most curious to see her naked).
Once we got home, we immediately opened up the magazine. No surprise, she and the other ladies were hot as you would expect, and while I felt a slight stirring of my cock, it wasn't at full attention, and as my friend said, he had a hard-on briefly, but that was it.
He asked again about the porn, so off to the closet where we kept it I went, and came back with a couple of tapes. The first scene to come up was an amateur clip of a girl and guy fucking outdoors. She had luscious tits and a hot shaved pussy, and he unloaded all over her bare lips. It was enough to get me hard, and while my friend watched intently, he said it wasn't keeping him hard.
On to tape two, a regular porn (with what passes for a plot linking the scenes together), that happened to open with a lesbian scene.
My throbbing cock was soon obviously joined by his, sticking out in his pants. It didn't take him long to start rubbing through his pants, and I followed suit. Mentioning how uncomfortable he felt, he first opened his zipper, then, eventually saying he needed to set it free, dropped his pants down to his ankles. Sticking out through his boxers was what I estimate to be a seven inch cock (about an inch longer than mine), that he immediately started jacking off.
Not to be left out, I took my own aching dick out and began rubbing it, partly at the sight of the hot oral action on the screen, and partly at the sight of him stroking himself off.
As the scene reached its end, he asked to replay it, which I quickly obliged. Encouraging the girls on the screen to, 'Eat that pussy!' he was clearly getting closer to release, as was I. Our pace quickened; our breathing getting heavier. As he started to moan, 'Oh God, here I go!' I was nearing my own climax. He leaned back, kept stroking furiously and finally released his hot cum all over his hand. That was all it took for me to shoot my own load, the cum pumping out of me feeling like it would never stop.
We took turns cleaning up after a few minutes, and so far, haven't had the opportunity to recreate that fun. I don't think he's as into repeating it as I am, so if not him, hopefully I can find someone to jerk off with again, soon.