I imagine that many guys had similar teenage years as mine - either I was pulling myself off, or planning how I could pull myself off.
One of the most memorable orgasms I had as a teenager happened very late one quiet Sunday night - I think I would have been 14 at the time. After everyone else had gone to bed, I lay in my bed with the lights out playing with my cock and getting worked up for a decent orgasm. After I'd spent some time playing with my erection, I started fantasising about how I wanted to come. For some reason that I really can't remember, I got hooked on the idea of being somewhere high and watching the come spurt out of my cock and fall some distance. I lay awake wondering how I could do this, and finally came up with the idea of climbing a tree. The only tree around that I knew I could climb without a ladder was out on the street outside our house - in public-but I was getting more and more turned on by the idea of climbing that tree and jerking off. Finally, I reached that state of horniness where the need to relieve the pressure in my cock overtook any sense of caution, and about midnight I eased myself out of bed, stripped, and quietly opened the outside door to my bedroom.
Fortunately it was warm outside, and I snuck out of my room and around the corner of the house and crept up the path to the road. There was a high fence running around our section so it was quite private, but the tree that I had in mind was about twenty yards around the side of the house on the other side of the fence, and I could only get to it by going out into the street and walking along the footpath. We lived in a quiet suburban back street, and it might have been the middle of the night, but there was a streetlight on the other side of the street, and if a car came along or someone was putting the milk bottles out, there was no short way back to the house, and I'd be caught. I stood in the shadow of the fence weighing the risks and quietly pulling away at my cock, until I could stand it no longer.
I walked quickly out onto the footpath: my cock was sticking straight out as I walked, swinging side to side. Walking naked in public was scary and turning me on at the same time. It seemed like it was many minutes before I got to the tree, but must have been less than a minute. I grabbed the lowest branch, and climbed up onto it. I climbed onto a higher branch where there was a clear drop below me, crouched on the branch with my knees spread wide, braced myself with my other hand, and grabbed a handful of my erection. I can still remember the feeling of my balls waving around in the night air as I pulled away at my cock. With all the anticipation it only took a minute before I could feel the pressure building, and I slowed down the stroking to hold off my orgasm. And then I came, and watching my cock spurting come into the air and it falling 10-odd feet to the ground was easily as much fun as I'd thought it would be. I waited a few minutes to get my breath back (and check that no-one was watching), and then I eased myself down out of the tree. I snuck back along the footpath to the gate, and back to my bedroom. The part of the memory which never fails to turn me on now was the sensation of the last few drops of come dribbling out of my now relaxed cock and running down my legs as I walked along the footpath. When I got back to my bedroom the realisation of what I had done hit me, but the image of my cock ejaculating into the night air was inspiring enough to make it worthwhile.
While I've had a few more outdoor sessions, none of them was quite as daring as that one.