Yes - my college roommate of four years. We became close friends very quickly and, as you might imagine at that time in our lives, sex was a frequent topic of discussion. After a few weeks we each admitted that we masturbated regularly and lamented the lack of privacy. One night after having a couple of beers, we went to bed in our respective bunks and turned out the lights. Out of the blue, he said, “fuck, I’m horny…I need to beat off.“ I chuckled and he asked, “are you going to jack off?” I said I probably would. We both proceeded to jerk off, not attempting to be quiet. After it was clear we both had cum, he asked, “did you have a good orgasm?” I told him I did, we both laughed and went to sleep. After that, we both masturbated after lights out fairly regularly - probably two or three times a week.
We compared our cocks once with the lights on. We were sitting on the floor one hot summer day, listenting to music. He said, “I’m horny.” I said, “let me see,” and he pulled his hard cock out of the leg of his gym shorts, and I did the same. We both looked at each other’s erect penises, laughed, then tucked them back into our shorts.
We both were really relaxed about nudity, as well. After showering, either or both of us would come back to our room and take our time drying off, walking around naked, picking out our clothes, etc. We both were fit then (and still are). He was (and still is) a handsome guy, with a long cock and big floppy balls.
We’re still close friends. I live in the city, he lives in the suburbs with his wife and kids, and we both lead busy lives. Even so, we get together every few months for drinks and dinner. Each time, it feels like no time has passed at all since our college days. We haven’t talked about all those times we masturbated together, but he recently told me that he missed those days of being roommates. He commented that we got along very well, were good friends, never fought, and really had a lot of fun. Of course, I told him that I feel the same way.
Of all of the friends I’ve had in my life, I am closest to him. Of course, I would love to hang naked and masturbate with him again - and I do long to do those things. While that’s unlikely to happen, I still cherish our friendship. I think we’re as close as we are because we shared that intimacy - being nude around each other and masturbating together. Taking those risks early in our friendship allowed us to be vulnerable with each other. That vulnerability exists between us today - we continue to share really personal feelings that we don’t share with others.