I have been a reader of contributions on the Solo web site for quite a while. I have enjoyed masturbating while reading the stories. I have always been a lurker and had never posted a story previous to this. I love the direction this web site is taking since the ownership change.
This is about an event which happened in my youth. I grew up terrified of women. I didn't have intercourse with a female until I was 20 years old, although there were plenty of earlier opportunities. My nervousness prevented me from taking advantage of those opportunites. I lost my virginity to my 35 year old night nurse during an extended hospital stay. Anyway, I'm getting off topic. This story is about masturbation.
When I was about 15 years old I used to masturbate with a friend. Although I was terrified of women I found it easy to talk with members of my sex. I was hanging out at Mike's house when the topic of masturbation came up. His parents and sister had gone out for the day so we had the house to ourselves. Mike asked me if I masturbated. I told him that I did. He asked if I would like to do it with him now and I quickly agreed to. Our cocks were very hard when we pulled them out. That's one thing I miss about being a young teenager. It seemed that I always had a hard-on and could cum many times a day.
Anyway Mike and I started playing with our cocks. He said that we should time it so that we both cum at the same time. That sounded good to me. Since I had always been concientous about make a mess when I ejaculated I asked him where I should shoot it. Mike left for a bit and quickly returned with a garbage can. We stood facing each other with Mike holding the can between us. He told me to let him know when I was ready to cum. I told him that I could cum anytime. He said let's cum now then. Pretty much simultaneously we both started squirting. Mike's cum dribbled out while I ejaculated about 8 to 10 streams into the can. I have always been able to shoot quite a bit, but especially so during my younger days.
We wiped off our cocks and discussed what we had done. I wondered why Mike's cum hadn't squirted out like mine had. He told me that it used to squirt out, but now it only dribbled. I didn't question this at all. I just figured that some people are different than others.
We were both extremely excited about what we had done and our cocks stayed hard. Mike suggested that we do it again. Mike asked me if I had ever fucked a girl. I told him that I hadn't. I was worried that my cock wasn't big enough to please a woman. I had been raised on pornography and tales of women screaming for foot long cocks. Mine was close to 6 inches and at that size I didn't think it would be adequate to please a woman. Mike said that he didn't think my penis was too small. As we stroked ourselves I asked him who he thought had a bigger one. Mike said let's see and walked toward me. We were facing each other and he grabbed both of our hard cocks, with his underneath mine. The peeholes of our penises were touching each other's tummies. Although mine might have been a bit thicker we were very close to the same length. We stepped back from each other and resumed masturbating into the can. Once again we timed it so we both ejaculated at the same time.
We stopped for a while afterwards to watch television or something. Laker Mike suggested we do it again. In those days I didn't have a problem getting hard or cumming, so we masturbated again.
Mike and I masturbated together many times after that until he got a girlfriend and our sessions stopped. We never progressed beyond masturbation. Mike had told me that once he and another boy had experimented with oral sex. I was receptive to trying it, but we never did. Another time Mike and I visited a girl I knew who had a reputation for being easy. We were sitting in her basement when I pulled her into my lap and she started rubbing my crotch. The scene had the potential for threesome written all over it, but I panicked and removed her hand. I very much wanted to be with a woman, but worried that my performance wouldn't have been very good and I would be laughed at.