Earl got me started.
Just after my fourteenth birthday, Earl came to live with us for three months. Earl was an engineering student who got a summer job at the same plant where my dad worked. He didn't have a place to stay so my parents offered to put him up for the summer. We had only three bedrooms in our house, my parents, my kid sister's and mine. I had a double bed so he bunked in with me.
Earl was 18 and an okay guy but our interaction was rather limited due to our age difference. I was used to having the odd relative bunk in with me over the years so sharing my room with someone else was not new to me.
Being a grown guy, Earl fascinated me. When it came time for bed he stripped down to take a shower. He was tall, really hairy and sported a very thick cock, rather short but really thick. At 14, I was well into puberty. My equipment was practically bald at that time although my shaft was about the same length as his, about 3 inches soft, maybe 5 inches when hard. Neither of us was circumcised. I had not started to jerk off because I hadn't figured it out yet. This was during the years before the internet. I was having wet dreams two or three times a month for the past year but I had yet to experience the glories of orgasm.
That first night I fell asleep before Earl came back from the shower. I guess I wasn't that soundly asleep because I awoke to a shaking bed. It was dark but I was aware that Earl was doing something on his side of the bed to make it move. (He was stroking his cock of course but at that I point I had no idea what was going on.) Into the dark I asked, 'What are you doing, Earl?' He stopped dead for a few seconds, then told me he was rubbing his sore thigh. I said good night.
A few minutes later I heard him whisper, 'Jimmy, are you asleep yet?' I was still awake but I didn't answer him and pretended to be asleep. Sure enough, the bed began to shake again. This time I slowly and quietly reached up to the headboard and turned on the reading light. Wow, what a surprise. Earl was lying of his back, completely naked. He had rolled back the sheet below his knees and was stroking his hard cock.
Caught in the act, Earl made no attempt to cover up or lie about what he was doing. He said he was 'jerking off'. He realized of course that I had not learned yet to stroke mine for pleasure. I hold him I had wet dreams and knew all about the birds and the bees. So he offered to show me how to bring myself to heaven's gate. Not that there was a lot to learn. Well, Earl immediately supplied the necessary details and within a few minutes I was on my way to my first orgasm.
I remember that first time, very well. Does anyone forget it? What can I say, other than it was an amazing event, feelings deep inside me that I could not even imagine were possible to experience. Semen spurted out of my cock and onto my belly. What an incredible, wonderful discovery!
Earl's eruption of cum made mine look rather feeble. Big spurts of cum shot out of his thick cock onto his stomach and chest. We both lay still for a few minutes afterwards. Then he reached for tissue and wiped up. I cleaned away the cum puddle on my belly. Earl asked me not to tell my parents or anyone else about this. Not to worry, not to worry. I shut off the reading light and rolled over to the nicest, deepest sleep I had ever had.
I soon got into a daily routine of jerking off whenever and wherever I could, often two or three times before bedtime. Earl worked shifts so often I was already asleep when he finally turned in. I quickly discovered one of Earl's routines for easy cleanup. He didn't let his cum fly all over himself like that first night. Rather he would reach for one of his dirty socks that he left beside the bed. He would shoot off into the sock, wipe up and toss it under the bed. When she did the laundry, my mom used to ask me to bring down the dirty laundry from my room. That first week I discovered that some of Earl's socks were really stiff with dried up cum deposits. I found my socks useful for the same purpose too.
Another technique that Earl taught me was to use lube. Although we both had foreskin, lubing up with hand lotion meant that you could jerk your cock head directly. The added stimulation is delicious compared with dry sliding the foreskin - it's more like real sex. Earl kept a bottle of lotion under his side of the bed and I availed myself to it too. Whenever we ended up in bed at the same time, we almost always jerked off together.
Very soon after the initial session, we began to jerk off each another. The routine was pretty straightforward. Earl always wanted to be done first so he would lie on his back on top of the sheets and cross his ankles. As we talked he would begin to pinch his own nipples which produced an almost instant hardon. Earl's hard cock was short, maybe 5 inches long but about 2 1/2 inches thick through. (At the time mine was about the same length but not nearly so thick.) I would lube up my fist and start twisting it around his cock head. Earl liked to cross his feet and lay back, fingering his own nipples while I did the twisting action on his cock. When he was ready to cum, he would reach for one of his socks to catch the semen.
Then it would be my turn for bedtime dessert. Earl never seemed very enthusiastic about doing me though. I think he just did it because he felt he had to. I always enjoyed his handwork though. He would grip my cock head with his slippery fist and make me cum very fast.
A few weeks after receiving my induction into the world of self-pleasure, Earl suggested that it would be nice to jerk off by rubbing against one another. I agreed. He had me lay on my side facing away from him, then lubed up his cock and slipped it between my legs. I kept my legs tight as I could. While pumping his cock between my thighs, he reached over and stroked my cock. Earl shot off a really big load that time. There was semen all over my thigh, my nuts and a big blob on the sheet. He didn't want me to do the same to him and quickly finished me off with his fist. I never got to do it to him. Although he did it again a few times.
Earl started going out with a girl who worked at the same plant that he did. There couldn't have been much sex (if any) between them because Earl continued to jerk off like there was no tomorrow. At the end of the summer they split up when he returned to college in another state.
All this took place a long time ago. Looking back on it today, I don't think Earl was really very interested jerking off with me. After all I was still a kid when he was already in college. But he was sharing MY room and MY bed and he got caught in the act by ME. So he made the best of it. As for our mutual jerk off sessions, I think it was the sheer enjoyment of it. And maybe venturing into territory that was a bit risky and taboo. Ditto for rubbing his cock between my thighs. I think Earl would have tried having sex with a knothole if he thought it would work.
By sheer coincidence I did hear of him recently. Last year the firm I work for hired a new accountant. She was fresh out of college. At our Christmas party she was chatting with my wife and me when she mentioned her dad. His name is Earl and he is an engineer. There aren't that many Earls around, so I asked a few more questions and she took out a picture of her mom and dad, taken when they were quite young. Sure enough, it was the same Earl who had introduced me to the joys of self pleasure over 25 years ago. Small world, isn't it?