Solo-ing through the high school years but almost doing it with friends. I wish now... I had.
This was small town, late sixties and I guess I was a good little boy.
I never talked about masturbation with any of my friends and never
did anything with any of them. There were almost two times though that
I now wish had turned out differently.
I remember one summer after the 8th grade when I went over to my best friends house. His parents worked shifts so instead of going to the door and knocking I went around to his bedroom window. I looked in and he was lying on his stomach on his bed, both hands at his crotch, and he was humping just like I did. I think this was before I learned to masturbate with my hand. I watched him for a moment and not wanting to embarrass him backed away and went to the door and knocked.
After a bit he came to the door and we talked or did whatever we did back then. I never told him that I'd seen him and we never talked about masturbation. I sometimes wish that I had the nerve to have joined him or at least talked about it.
The other time was about a year later.
Another friend was telling me about a sleepover that he'd been on with
a mutual friend. He told me that the friend asked him if he wanted
to play milk the cow and then pulled out his penis. My friend said he
ran out and asked to be taken home. I never had a sleep over with my
friend's friend but I often wonder how it would have gone if I had and
he'd asked me about milking the cow.