As I entered my teens, I started realizing that playing with myself felt pleasurable. Along with this I noticed certain stimulation would cause erections. Putting two & two together, I started experimenting as most young boys do around this time. Rubbing my hard-on felt really good, but not knowing that there's a payoff at the end. That is to say I never did it to the point of orgasm.
I should also mention that the reason for my ignorance was growing up in a very conservative home, in a small farming community out in the middle of nowhere. So the topic of sex was never broached & so I was left to figure a lot of things out for myself. Fortunately, I had a really good friend I went to school with - Kevin (name changed for obvious reasons). Being both the same age, we grew up together and so by the time of our teenage years, we were fast friends.
So naturally we started discussing masturbation as part of our regular discussions, because Kevin too had started noticing the same things as me. During break we'd find a secluded corner and talk about how good it feels, how hard we'd get when we were touching ourselves... which at least for me just got me horned up! One day we were talking about the same thing, when Kevin asked whether I've ejaculated. I'll admit, I had no idea what he was talking about. Noticing my confusion, he explained that when I was playing, I should keep going, that eventually I'll ejaculate and that it felt really good. This naturally lead to an in-depth discussion of jerking techniques - how we both hold our cocks, how fast\slow we go etc.
So that night in the shower, I sat down and started playing with myself, only this time I incorporated some of Kevin's ideas - gripping my hard cock in the palm of my hand, rather than just rubbing on it with my open fingers. I also made sure to move the foreskin up & down over the head (we're both uncut). Doing this for a few minutes, I started feeling a new sensation... a tensing up of my body, not least of which was happening in my balls. Then in a sudden burst I felt a wave of pleasure wash over me & at the same time started blasting several ropes of sticky cum onto the floor of the shower. I just successfully brought myself to orgasm for the very first time! Getting up off the floor on shaky legs, I made sure to clean up the mess while thinking to myself "I can't WAIT to tell Kevin tomorrow".
We had a some great experiences in the years to come, but those will keep for another update.
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