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I began masturbating before I knew what I was really doing. Just that it felt good to grind my cock on my pillow, it was soothing, and it helped me fall asleep. I didn’t really know how to cum yet, but it still was a nightly occurrence. My mother discovered this at 18 and, rather than discourage me, she would tell me it was natural, and that she was happy it made me feel good. She even made it part of our nightly tuck in routine, showing me how one of my stuffies could feel even better to grind against than a pillow, and then giving me a backrub each night as I humped it and she told me what a good boy I was. It wasn’t until later that I picked up on the fact that she was masturbating too, and usually would cum at the same time my body would shudder and I’d collapse into sleep. But eventually I became aware enough of the change in her breathing and her moans when I moaned that I started to pay more attention to the fact she was fingering herself. As my masturbation habit became larger and I started to leak, and eventually shoot gigantic cum, she used to put her hand at my head to tickle the cummies out and catch my mess. She’d then take my cum and masturbate it into her pussy until she came too. As I got into being a bit older still, and was a bit more shy about it all, she’d discover other methods to encourage me, including getting me dirty magazines, reading me dirty stories, and even masturbating my ass with the tip of her finger to put me over the top. Every time when I came she’d tell me what a good boy I was and tell me how big and manlike everything was becoming. It tapered off once I was 22 and moved out but even now it’s that imagery and wanting to discover a mommy type to do the same to me that makes me cum.

NSFW: yes

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