I've been asked more than once, over the 5+ years of writing this blog, how to get a buddy to engage in masturbating together. Well, it pretty much happens as I described an exceptional encounter yesterday: The best way is to let it happen (sort of) spontaneously.
Or, as happened with my first bunk mate in the military. I walked in my first night of the assignment, he was lying on his bunk flipping through a magazine and stroking his cock. He wasn't the least bit shy. He not only continued his self-ministrations, he told me it was his nightly routine; I could either go somewhere to pass the time or, he pointed me to his porn stash, join in.
About a week later, as we were kicked back on our bunks and enjoying ourselves, we both ceased trying to sneak glances. He laid there and watched me. I looked over to watch him.
He stood between our bunks. I stood to face him. He reached out and I let him wrap a hand around my cock. I reached out and wrapped mine around his.
But, if you want a current friend to become a jack-off bud, the best way is to introduce it in a non-threatening manner such as talking about sex, or surfing and watching,
or reading porn,
Or, let him walk in on you
invite him to join in, and let the natural physiological response lead the way.
In other words, you can't be ashamed of your cock getting hard,
you can't be ashamed of groping it,
you can't be ashamed of dropping trou.
And enjoying yourselves together