how often should boys pleasure themselves?

Most guys do it every day. Some do it more.

A very good question. Since I was a boy wants and have raised boys I know a bit about this subject. Regretfully I did not have a very good father so he did not teach me about anything, including sexual topics. I know that I learned most of what I needed from my best friend. During puberty I would pleasure myself quite often an estimate sometimes three times a day. My friend and I were very open with each other and were able to camp out and would talk about things like masturbating, which we sometimes get together and of course we talked about girls. I raised 2 boys and I committed to be there for them and unlike my father would talk to them about anything they had questions about. When I was a teenager I was lucky enough to have an uncle that I live with for some time and he absolutely led myself at his home. He had an adopted son named Josh, was about seven or eight years old when I was about 16 years old. One day I realized that after my uncle took a shower and helped Josh take a bath that they would just hang out in their underwear and watch TV and he told me I was welcome to do the same if I wanted to. He was Very open to letting Joshua be naked if he wanted to. We would also read a lot of swimming in the pool naked. Although I knew the basics about how to get an erection and how to masturbate my uncle was open to talking about it with me if I had any questions. When my boys were young I decided that I would let my home, the privacy of my home, somewhat of a place where my boys could go naked and I as well and my wife. When my boys reached or started reaching puberty that were not at all embarrassed to show off their erections and I guided them through knowing how to masturbate and letting them know that it was completely normal. Like me when I was a boy the two of them would pleasure themselves often throughout the day even and I never scolded them on the bill sharing. It is quite natural, and boys love to do it, to toss themselves to be able to get an erection. Fathers should always teach their sons to never be ashamed or embarrassed of their bodies, to be able to strip down if they chose, and appropriate private places that is. There were also times like after swimming at a beach that I took my boys to the showers because in a way I wanted them to see other boys and men of different body types and enforce that being naked around other males was perfectly fine. With a few exceptions that is.