When I was 14, my older brother was 16 and everyday after school we would be home alone until my parents got there.
On one particular day, we happened to be joking around about him jerking off all the time because he couldn't get laid, to which he ended up pulling his dick out and shaking it at me. I was surprised because I had never seen my brother naked before, or any guy for that matter.
We went separate ways in the house, and eventually ended up watching television together later that evening after my parents had got home. We would watch television in the basement and my parents in the family room above us. We were joking around like we always did, particularly about sex, which had become a frequent topic of our conversation. Then a huge breasted woman came on the television and jokingly I asked, 'Would you like to be alone?'
He looked over at me, grabbed my hand and stuffed it down his pyjama pants in one swift motion, but I pulled it back out slightly brushing against the side of his penis. He said, 'No, you can stay and do it for me.' Then he laughed and grabbed my hand again, which I tugged away again, laughing too. We wrestled like that for about two or three minutes, until he got my hand back into his pyjama pants. To my surprise he was almost fully erect. He held it there, rubbing the back of my hand against his dick. I ripped my hand out again and said, 'Perv!'
At this point, I was more turned on and curious than disgusted and honestly hoped that he would proceed until I could drop the hard to get routine. I moved over to one end of the couch, and he moved to the middle cushion, right beside me, holding his pyjama pants open. His shirt covered his erection, so he pulled it out of the way and for the first time in my life I saw an erect penis.
The Head was gooey from pre-cum leaking out of the piss slit and he was about six inches in length. He said, 'Touch it.' He pulled his pyjama pants down off his butt and leaning back against the couch grabbed my hand again. This time he positioned my hand so that it was gripping his dick.
He moved it up and down a few times and let go. My heart was pounding out of my chest and though I don't remember, I guarantee my panties were soaking wet. I could hardly catch my breath and my legs were shaking. I began and slowly rubbed my hand up and down the length of the shaft. He repositioned my hand saying, 'Hold it like that'.
I positioned myself side ways on the couch, looking directly at his penis. I continued to stroke him as he said, 'Faster!' He closed his eyes and my crotched was throbbing as I increased the pace. A minute later I was rubbing as fast as I could when I felt his penis jump and his breathing become coarser. I looked at his face to see him tightly holding his eyes shut. He pushed his pelvis forward in my hand it jumped again, as he slightly humped with my motions. I went as fast as I could and it happened.
He came in thick white spurts all up my wrist and arm. It also landed all over his pelvis, with the first spurts landing on his shirt. He let out a sigh, stopping my hand from rubbing, pulling his pyjama pants up and stuffing his dick inside.
I wiped the cum from my hand and wrist on the back of the couch. Then I went upstairs to my room, where I masturbated and came in about 30 seconds, to the best orgasm of my life.
After that day, this became our daily routine. I doubt he ever even jerked off alone anymore afterwards. Sometimes I would make him cum two or three times and I remember on one occasion making him cum seven times in one day. After school or while we were watching TV, my brother would grab my hand and shove it down my pants, initiating it and I would jerk him off until he came. It lasted for about a year and my parents never caught us, though sometimes I would be jerking him off just one room away from them.
In that time, I would have my first orgasm in front of a boy. It got to the point where I would cover my lower half up with a blanket while I jerked him off. I would masturbate with my left hand, while I masturbated him with my right. I never let him see my pussy, but through time I did let him play with my breasts and I even started masturbating under a cover while he was in the room. I did this after I had finished jerking him off, as before that I had normally finished myself in my room.
When he turned 17 he got a girlfriend and we never really talked about it after.