Like most boys, I was always very furtive about masturbation. I started doing it when I was 7 or 8, and it was one of my favorite activities. My father died when I was young, so I was raised by my mother, who was always very supportive and understanding, but she never mentioned sex to me in any manner. I was left to discover masturbation and figure out what it was on my own. I don't know where I got the idea it was wrong, or nasty, but I had that impression, so I hid my activities under my covers at night or out in the woods behind our house.
One day when I was, I think, 12, I had a major revelation. I thought my mother was out of the house for a couple of hours with the lady next door, so I lay on the couch in the TV room and was having a nice session with myself when my mother walked in on me. I was mortified, and struggled to pull my pants back up, falling off the couch in the process. My mother had this horrified look on her face, so I thought the confrontational was going to be awful. I had visions of major guilt, scolding, accusations, etc. But I was hugely surprised that her reaction was very different. She apologized profusely for walking in on me (how could she know?), and more to the point, for not discussing masturbation and sex with me. She was upset that I obviously thought I was doing something wrong, and quickly set me straight. She said it was perfectly normal and healthy, that all boys (and most girls) did it, and I shouldn't feel embarrassed about it. I was completely taken aback. She said she realized that without a father, it was her job to teach me these things, and she'd kept postponing it. She even told me she did it a couple of times a week in order to keep her sanity. I didn't even know that women did that, so that was quite a surprise.
Needless to say I felt a lot better, but it was still hard to talk to her about it, I guess since I was so conditioned to feeling guilty about my habit. She said she could understand my reluctance, and asked if I'd feel more comfortable talking to my uncle about it. I said yes, not really knowing if I could do that, so she set me up with a chance to talk to her brother when he came over the next weekend. He sat with me in the TV room and we talked about stuff for an hour or more. He explained how he'd learned about it, how he did it, how often boys do it (I was normal!), what I could expect as I grew older, etc. That afternoon, with my mother's concurrence, he installed a lock on my door, provided me some educational books on sexual development, and gave me my first tube of lube and a large box of kleenex. He told me he and my mother were going to go shopping, and he expected me to masturbate to my heart's content while they were gone.
They were gone for about two hours, and I alternately read the book and jacked off. I had three wonderful orgasms while they were gone -- the first guilt-free orgasms of my life. I was tired but relaxed by the time they got home. When they came in, they asked me if I'd had a good time, and I said yes. They said that was great, and I no longer had to feel like I had to hide my activities.
From that time on my mother would joke about it, and I felt free to jack off whenever I wanted to, as long as I had privacy. The lock on my door saw to that. And my uncle slipped me softcore porn every so often, which was a lot of fun.
My life was a lot more fun after that incident.