When I was dating my wife, we lived overseas. She always told me she thought I would get on with her brother, whom she thought was gay.
Well, I did finally meet him and we did hit it off. He kept hinting to us that he might be gay but never quite came out and said it.
As our friendship grew, we discussed personal matters. One day he was talking about how some guys experiment. I flat out asked him if he ever had. He replied that he had back in college.
I then asked him if had more recent experience and he said 'yes'. Then he turned the table on me and asked if I had. I told him I had jacked off some years before with a close friend.
Well, soon after, he formally came out to my wife and me. After he left, my wife asked me what experience I had with guys, and I told her about my previous jack off encounter. She asked if I had ever tried anything more, to which I truthfully replied 'no'. To which she retorted, 'not even in college?'!
Last year, her brother and I really started hanging out together and are as close as two friends can be without it being more than friends. He is pretty shy and modest, and seems unaware of just how good looking he is. I was pleased when he felt comfortable enough to work out with me, and for us to get naked together in the locker room.
He is uncut, I am cut. I told him I was alway interested to see how an uncut cock works, like the foreskin retracting, etc. I finally worked up the courage to tell him I'd like to jack with him and couldn't believe it when he said 'no'.
We continued as close as before but I just could not get my head around it. Later, he would tell me that he said 'no' as I caught him off guard and he could not get his head around it then.
Well, a short while back, he and I were together. He was just breaking up with his boyfriend, and was planning to hook up with a guy he knows later that night. As we sat on the couch, he discussed his recent sexual activity in such detail that I got hard.
He could see it through my pants, and I began at first to cover it, then to stroke it, with my hand. H kept going on and I slipped my hand under my pants, asking him if it was OK. He said it was, but reminded me he was meeting a guy later so mightn't be able to do much with me.
I said, 'would you at least show me'? He smiled, and said 'I suppose its nothing we haven't seen before'. We stood up and took our pant off, then I lowered my briefs, he lowered his boxers. We were both semi hard. We showed each other around our cocks, me showing him my circumcision scar, him showing me how his foreskin goes back.
He said he'd never gotten hard with a friend before. We then began to masturbate ourselves. By this time, we were very close, side by side on the couch.
After a while, he said he'd better ease off. I asked if it was OK if I finished up, and he said 'yes'. He kind of flicked his cock as I began to get some precum. His eyes totally locked on my cock as I came.
I thought it might be awkward after, but we were fine. I cleaned up, we put our cocks away, and chatted, looking each other in the eye, for an hour after. I told him I'd wanted to do that with him since we'd first met.
When he left, we hugged. I wanked off three more times that night.
Some time later, after the three of us had been to lunch, my wife told me she knew something must have happened between us. I asked what made her think that, and she said that neither he nor I could hide the easy interaction between us. She said you don't get that just from being regular friends.
I'm very lucky. Growing up, I never thought that I was or would be.