I grew up with several older sisters and an older brother. Consequently, privacy was at a premium and sightings of body parts of every age were a common sight. I was taught to play doctor by my brother, with my sisters. They had prominent clits which stuck out through their lips, which set some of my personal preferences for life. The neighborhood girls were also co-operative and by the age of eight I had tickled and probed several pussies. This also left me addicted to the smell, texture, and taste, of pussy. But I knew nothing of masturbation or why my dick felt so good when it was hard and rubbed against the sheets of my bed. Girls weren't interested in playing with boys ugly dicks but loved having their's played with.
The summer I was twelve, two of my buddies (we'll call them Jimmy and Dan) were over and we were talking about girls from our swimteam and what we thought their pussys' might look like, when Jimmy said he had to show us something. We were in our huge backyard sitting in one of the old cars my dad liked to buy and fix up. Jimmy was in the back seat. He told us to stay in the front and only look back when he told us. We heard funny noises coming from the back seat and when Jimmy shouted for us to 'look quick' we turned to see him with his hard dick in his hand and white stuff oozing out the piss hole. He said thats jizz, the stuff that gets girls pregnant. We had heard of jacking off but didn't know what it was. Jimmy said he had just jacked off and we should try cause it's incredible. Danny and I both said no and Jimmy said 'Look I'll do it again and you can watch this time.' So he did it again and this time we watched as the cum spurted out of his little cock and dribbled down his fist. That was really neat, so we both pulled out our dicks and started pulling. It felt good but nothing was happening for me, so I stopped. Danny tried, but he too stopped and said maybe he'd try later.
That night I slept over at Jimmy's house. His room was usually shared with his older brother, who was away and had some magazine centrefolds on the walls. I'd never seen one before and found myself with a stiffening dick. Jimmy asked me if I had jerked off yet and I said no. He said I bet you feel like it now, I said I'd try, but I got nowhere. We were laying on his bed with our pyjamas around our ankles and our dicks in our hands. Mine was significantly longer and thicker than his and he stopped to look at mine as I tried in vain to cum. He said 'look I know what to do, let me try'.
So he grabbed my cock and said boy are you ever hard your gonna shoot a load, your balls are huge too, this is gonna be good. As he stroked he talked about the naked women and their huge tits (no pubes in those days) He told me his brother shot big loads and sometimes hit the ceiling. By now an amazing feeling was taking over and I felt like my cock was a barber pole with something swirling up my shaft like the colours on the pole. I started to get dizzy and was about to scream. Jimmy slowed down and said he could feel my cum starting up my cock (my cock really swells as I get close and my wife says she loves it and feels it inside when we have sex) and I should watch my cock. The slower pace intensified the feeling and I had to stifle my cry as a huge jolt of cum shot out of me for the first time and splatterd on the ceiling, then as Jimmy laughed and continued to stroke me, my cum hit the headboard and the wall. The feeling was incredible, I didn't stop coming for several seconds as my balls churned out gob after gob of creamy cum. Jimmy put his hand to my mouth and said as it was my first cum I had to lick it off, so I did, I was so high I didn't care. Jimmy said that was great, the most he'd every seen, and started jerking himself off to a big cum. I tried again and this time succeeded for the first time, it was almost as good as the first one in some ways and better in others, as I was in control of my cock this time. My cum shot out but not nearly as much or as far. We licked off our hands as our new tradition and went to sleep.
In the night I woke up as I felt my cum spiralling up my cock again. Jimmy's hand was sliding up and down slowly on my cock. I let him finish as I shot cum up to my face. I returned the favour, stroking his small cock for the first time and really enjoyed the power I felt controlling his cock and making him come, I gave him my hand to lick off and fell back asleep.
I have no idea how many times I jerked off that summer with and without Jimmy, but it was several times a day, every day. My sisters and mothers body parts took on a new meaning for me as I soaked my sheets and underwear every day and night. I used to get full views of their hairy pusssies and small tits and took full advantage. One of my favourite techniques was to go back to that feeling I got from my bed sheets and I rubbed my dick head back and forth on the cotton. I found out after doing this several times in one night that if you do it too much, blood will come out as well as come. I also learned that if I lay on my side when I came, only a small amount of cum came out and I could jerk off several more times before running out of ammo.
Jimmy and I used to have contests and see how many times we could come in a row. At that age recovery time was non-existant and blisters were common. We would read dirty books together or look at his dad's magazines. We got his sister to join in one day but that's another category. We remained friends through school and sometimes jerked off together after that summer but that was the summer of my first orgasm.
I still love to masturbate and often have my best orgasms that way. My wife likes to jerk off too but we don't share that often.
Thanks for reading and I'll be writing some other stories for other categories soon.