Someone asked about this topic from me, so here goes, my perhaps rather unique experience.
My first masturbation experience occurred when I had spent a two week holiday in Europe, on the island of Crete. Towards the end of the trip, I fell sick, but soon recovered feeling well again (in my opinion) at the time we got back home. The doctor still ordered me to stay in the hospital for monitoring, for reasons I cannot recall perhaps there were signs of infection or something. Since I was quite well, I was immensely bored and wanted to get home quick, but was not allowed to. I spent 4 days there in total I think. I shared my room with a boy two years my senior; I have no recollection what his reason for staying there was, though, or even if I ever learnt it.
We did not get along very well at first, as he drew to himself whereas I, bored, tried to talk to him and play something wtih him. He just ignored me for what I can remember.
I think it was the second night, could have been the first as well, when I woke up in the middle of the night feeling this weird pressure or ache in my pelvis and penis. I had a hard on, which was not new to me, but this one felt extremely 'hard', painful, even. My whole middle section 'vibrated,' if you will. I remember that my head felt dizzy and my ear lobes were scalding hot and I could feel my heart beat in my head as if I had been exercising very hard. What ever I had dreamt of, I cannot recall.
I got quite scared. I thought I might be dying even, that I had really, really fallen ill, but dared not press the button to call in a nurse due to my painful hard on, which I thought she would inevitably discover. So, instead, I turned onto my stomach and just pressed my eyes shut and wished for the ill feeling to abade so I could fall asleep, or at least lose the erection. But it did no good, as the feeling only got worse and I was now having some serious pain in my pelvis and my heart was racing. I think I decided I need to call for a nurse, my hard-on notwidthstanding; but ere I could do this, I had what I later learnt my first orgasm, which just exploded while I was reaching for the button. It lasted a good while, I think, and felt as if I had gotten an electric shock in my penis, only the shocks came in intervals. I may have cried (as in tears) a little out of fear, but as the peak subsided, I started to feel really good, and the pain gave way to immense calmness. I could not ejaculate at that age, so the orgasm was 'dry.'
Once it had fully subsided and my breathing was back to normal, I rolled on my back and studied my penis, which was still hard, but the pain in my penis and pelvis had dissipated and calmness like I had never felt before came over me. My roommate was fast asleep and had not noticed a thing. I wanted to go to the bathroom to further examine myself but, alas, I fell asleep as a result of the fabulous gentle calmness about me while wondering what had just happened.
In the morning I found nothing amiss and was content that nothing bad had become of the night's occurrance.
Feeling releaved, I went to brush my teeth while my roommate was taking the shower. I saw he had an erection, perhaps as a result of his showering his penis, and I quipped him I too had my dick go stiff at times. He laughed at me and asked what did I know about such stiffies, and having been treated in a somewhat demeaning fashion by the 13yo, I haughtily told him what had happened at night. He asked me didn't I know I had cum (what ever word he used I don't remember) and I explained I had been quite overwhelmed by it and had been worried I was going to die. He found this quite amusing, but did not mock me for it, but rather went on to tell me there was nothing wrong with me and that I could bring such a feeling upon myself at any time I wanted by jerking off.
We discussed the matter after his shower and his whole attitude towards me somehow changed after my revelation of my nightly orgasm. Later on in the day as we were killing time after lunch before the parents would arrive for that day's visit, he invited me to take a walk with him outdoors in the qudrangle, where we were allowed to go freely. He talked to me like I was his coeval and peer and no longer belittled me. I must say my self confidence was quite boosted by having been accepted by an older boy as a pal and having experienced a hus-hus 'guy' thing.
In the evening after we had gone to bed, he asked me if I wanted to learn how to do 'it', and sure I did, and he showed me, and I then followed suit. That is how I masturbated for the first time. He treated me very gently and kindly, like I was his little brother. It was a very positive experience for me.
Afterwards, when we lay in our beds, he suddenly told me about his mom, who had passed away a year earlier, and how he often saw dreams of her and that he still cried some times. I had been somewhat annoyed at my mom on the phone as she still called in the evening and I felt she was making all too many and quite unnecessary enquires throughout the day regarding my well-being. The boy told me I should not be annoyed at my mom for that and I never forget the way he said that.
I was free to leave the next day, but he still stayed. I have no idea what his reason for being there was. He seemed healthy to me, and he had to give the same samples I also did. Also, I was not annoyed at mom when she kissed and hugged me very publicly before we left.
I started masturbating regularly after that incident.