Don't know if my family is weird but my mom would quite often encourage masturbating. She'd always say it's healty and a very good stress reducer.

My sister who is three years younger than me and I always thought it was weird but our mom is very open about sex. When I turned 13 she talked to me one night before bed about puberty changes and of course masturbation. She used a banana and two apples to represent my penis and balks she said. She talked about the changes it would have, how to check my balls for cancer, and even stroked the banana talking about masturbation benefits. I was 13 so I was super embarrassed. I was in just my white briefs when she was talking about that and of course I got hard. She saw that and said see, your erect as we're talking about this. She gave me a bottle of lube and said if you prefer this, this is the best to masturbate with. Unfortunately I didn't masturbate that night.

The next night after school I was in my room at night, had dick out the fly of my underwear and was playing with myself. Of course my mom walked in. She saw and said oops sorry, I leave you to it. So I started doing the motions my mom described and within a minute I came. It was a new intense feeling. My briefs were cum soaked and so was my stomach. I cleaned up and my mom came back in a little later to tell me good night. She saw my dirty briefs laying on the floor and went to pick them up. She could just smell then from a foot away saying I guess it all went well! She told me don't be afraid to use your underwear to clean up with, they are white and they get bleached any ways.

Over the course of my high school years there were days my mom would tell me in the morning I should masturbate before school to help me stay calm during tests. When I was taking my graduation tests my mom had me wake up early so I could get ready fir school and study. By the third day I was stressing and I rubbed one out before leaving for school telling my mom I pit my briefs in the hamper and they need to be washed. She knew what I meant. But I found out masturbating that morning helped keep me calm