My first experiences of masturbating were at a younger age. We moved kind of frequently while I was growing up which helps me place my age. At first, I wasn't able to have an orgasm, but I remember thoroughly enjoying just the experience of having an erection. I would stand in the bathroom and rub my little hard, hairless cock against the sink, I'd try pushing it in between the radiator bars. I didn't get very far toward an orgasm, but I remember being so desperately horny that I almost felt pain in my stomach-visceral desperation! Even so, I loved it!! I had my first dry orgasm. I couldn't ejaculate of course, but I would get a very intense sensation and the tip of my cock would become incredibly sensitive and ticklish.
I first had an orgasm from humping a pillow. We had some large home-made pillows. One of the seams developed a small hole that was just big enough for me to thrust my little hairless cock into. I would hump that pillow at every chance I could get.... usually when I would get home from school while I could have the house to myself. Bliss.
It wasn't long until I realized that I could use my hands to achieve the same result. Now I look back and I'm shocked that it took me so long to discover that I could masturbate with my hands. None of my friends ever spoke about masturbating at that age, so it was pure self discovery. Anyway, what a revelation. Eureka!! At that point, my masturbation frequency sky-rocketed to once or twice a day on most days since this vastly increased my masturbation territory.
This was before the internet, so I had no clue that all of my other friends were probably also masturbating a lot. I was a little ashamed of my avid masturbating, so I never talked about it with anyone. Then with high school approaching, I thought to myself that I should stop. It would be too humiliating if I was ever caught by any schoolmates. Yeah right! Of course I didn't stop and my frequency must have increased if that was even possible.
I can't remember exactly when I first ejaculated, but that was quite a thrill to watch cum spurt out of my cock. Of course, that posed the clean-up problem. I would use one of my old socks when I masturbated in my bedroom (almost every night)... It got rather fragrant, as you can imagine, so I would sneak it into the garbage once it got too bad.
That was when I also became daring enough to masturbate in public. Usually late at night at a playground that was set back away from the road. I would strip naked and whack away! I would also go down to a lake that had a fairly secluded beach and skinny dip...well, I would swim for a bout 10 seconds before I couldn't resist rubbing my hard cock and shooting ropes under the water.
I'm married now, middle aged and still enjoy nice long indulgent masturbation sessions whenever my wife is out of town or sometimes when she is off spending time with her friends (no kids yet). She just so happens to be out of town right now, so guess what I'm doing tonight?! I have a nice raging hard-on just from typing this. Time for a nice long session... probably a few hours.