Everything has to start somehow or somewhere. My education into self pleasuring started at a very difficult time in my young life. My mother remarried an Irish guy who succeeded in getting me packed off to boarding school within months. Far from home and terribly depressed I did not know how to act around the other guys and I withdrew into myself. To make matters worse at 12 I was placed in a room with a 16 year old boerseun with whom I absolutely had nothing in common. It was a very lonely time for me. I struggled to sleep and lied awake nights on end. At 1st I did not notice but every so many nights I would hear my room mate making "funny" noises from his side of the room. I wondered what was going on and one very vocal night I incorrectly surmised that he was also unhappy and that the noises I heard was him crying or something. I sneaked over to his bed to see if I could comfort him and to my surprise saw him pumping away at his engorged cock. He did not see me and I was even more shocked when he came with a sigh of relief. I sneaked back before he saw me and lied awake for hours wondering what the hell I had just seen. It seemed naughty but so good at the same time. For days afterwards I tried to mimic him when alone but just could not get the same result. My cock got hard of course but no more than that. Let me state that at this stage I had never jerked off or even realised that what a hard on was for. I waited and one night I heard him wanking again. I again sneaked over and as I drew near to his bed, he came again. I pushed ahead and innocently asked if he was ok. He of course was shocked and embarrassed by what I had seen. But his stomach and had was covered in cum and he was struggling to clean himself without me seeing. I asked him what he had been doing and he responded "fok man weet jy nie wat tos is nie". I said no to which he laughed. I was disappointed that he laughed at me and I think he saw my confusion because he then told me to come sit by him. he calmly tried to explain to me what wanking was and how to do it. I must admit that I did not pay a lot attention as I was distracted by his flaccid cock lying in a pool of cum. He realised I was watching him and it excited him. Soon his cock was hard again. Fat and thick, throbbing with a life of its own. He asked me if I liked what I saw. He asked me if I wanted touch him. I did and I did. His cock was hard and smooth at the same time; and a little sticky from his drying cum. He asked me if I have ever wanked to which I replied not with much success. He told me to strip and then took my cock in hand. He rubbed a little and soon I had a hard on. He then started wanking his cock and told me to follow him. I watched him and soon I could feel an orgasm building. I stopped out of breath, a little scared about what was happening. He kept going and soon blew another load. Seeing my struggle he then grabbed my cock again and started pumping away. It was awesome and soon an orgasm was building again. Afraid I begged him to stop. I did not want to pis all over his hand. He just laughed, pinned me down and wanked my cock to orgasm. It was the most unbelievable feeling I had ever had. That night, after I promised not to say anything, I slept like a baby. Soon we were wanking 3 - 4 times a day. In the morning when we got up, In the afternoon after school. In the showers and at bed time. The boerseun took great pride in teaching me and together we learned new techniques. Another bonus was that as we were spending so much time together I met his friends and actually became quite popular. Sometimes we would wank in a group but we always shared our wanks when we were alone at night. It was a sad day when he moved on and left but I never forgot what he taught me.