One of my best friends and I, (his name is Ike) have masturbated ever since we were ten. We began masturbating with each other around the age of twelve. At that age, we had only our little pecks, very small amount of pubes and didn't come yet.
One day when we were twelve, he was telling me how his mom helped him masturbate. I was totally astonished, wondering why my mom didn't. He said that if I slept over at his house that weekend, his mom would probably catch us masturbating, and help us out. Ike lived only with his mom, since his parents were divorced.
And so, I went to sleep over at Ike's, one weekend. He said his mom was totally OK with masturbation, and he didn't even have to close the door or anything like that.
So one night, we began to masturbate in his room. We knew his mom wasn't yet sleeping, but pretended to think she was, so it would look like we would be caught totally unexpected. While we were jerking off, Ike's mom knocked on the door, and opened it, without waiting for an answer. She caught us redhanded, and we pretended to be surprised. She then said, 'Oh, I'm sorry, boys. It's OK, just keep going. I was just checking on you guys, on my way to bed.'
She looked at Ike, who then looked at her, and she realized that she had to help us. Ike's mom asked, 'Would you boys like some help?'
We both nodded. She took us both to her room, and began jerking both of us at the same time. It was awesome! She then got some lube, and speeded up the strokes. We came really quickly, and she said, 'There, all done! If you guys need my help again, just call.'
I was totally amazed! I could not believe, that Ike's mom had just jerked both of us off!
We continued being helped by his mom almost every weekend until we were about 15 years old. Now, just the two of us jerk each other off at least twice a week.