A true story of the first time I masturbated. At first I called this story "Dan and I" and it was to be about my experiences with my best friend. It ended up extremely long so I've broken it down into several smaller stories.
I shared a room with my older brother Lee for as long as I can remember and we saw each other naked daily. When he went through puberty he kind of flaunted it and would tease me for my small penis and lack of hair, waving his erection back and forth after he showered. I knew in a few years I'd go through the same thing so it never really had an effect on me. After a while his seemingly perpetual boner went away so I figured it was part of growing up.
I eventually started getting hair and growing. Also having erections all the time and seemingly for no reason. Every time I showered and washed it, it would get hard and tickled easily and seemed so sensitive as I rubbed soap all over it. While it felt good I never had the idea to just keep washing it and enjoy the sensations.
After showering one night before bed I went into our room and dropped my towel to put on some underwear, still boned up from the shower. Lee noticed and said something to the effect of "You're so hard it looks like it hurts.". I agreed and said I was sick of being hard all the time and was hoping I'd pass through this phase of puberty quickly. Lee didn't understand what I meant and I said I remembered how he was hard all the time and then after a while it stopped. Lee told me I wasn't jacking off enough then and that would help.
I'd heard talk about jacking off but really didn't understand it and asked how that had anything to do with my erections. He said if I played with it long enough I'd orgasm and my boner would go away, and if I did it enough I wouldn't get hard so often. Still confused I asked how you did it and he said I must have noticed him doing it after we had the lights out. Well, I hadn't. Once my head hit the pillow I fell asleep quickly and slept like a rock. While I had noticed some rustling from his bed and quiet moans from time to time I thought he was dreaming.
Lee said he thought maybe I was faking sleeping and our Dad had mentioned to him now that I was getting older maybe he should be more open masturbating so I'd figure out how to do it. And if that didn't work that Lee should just show me how and that tonight would be the night.
Lee explained that if you slid your hand up and down your penis for a while it would feel real good, better than washing it in the shower, and eventually you'd trick your body into thinking you were having sex and you'd have an orgasm and your semen would squirt out of your penis. With that said he went to his dresser and pulled a bottle of hand lotion out from under some clothes and pulled off his briefs. He started playing with his soft dick to get it hard and sat on his bed, patting a spot next to him motioning me to join him.
So I sat next to Lee who was now hard and he explained that while you didn't need lotion it just made it better and he squirted some on his dick and rubbed it all over. He handed me the bottle and told me to do the same so I did. He then said since I was smaller than him to just use my thumb and a few fingers like he used to do and slide them up and down, giving me a demonstration on his own larger penis. I copied him and it did feel good. Lee then said it would take a few minutes and not to stop, even if I felt like I had to piss. He was stroking his own using his whole hand and then said to rub around the head from time to time like he was doing so I tried that too. Damn it felt good.
We both sat there stroking and I started feeling things I never felt before. It was like electricity was in my pelvis and I started breathing harder and Lee told me to speed up my stroking. I couldn't believe the involuntary actions my body was having and I lay back on the bed. I suddenly felt like I had to pee but remembered Lee told me that would happen so I kept going. Suddenly my hips started thrusting upwards into my fingers, I couldn't help myself. Lee said "Here it comes" and I felt spasms in muscles I didn't know I had and this stuff started shooting out of my dick. Straight up and back down on my hand. It felt so hot. And the feeling of my first orgasm was amazing. Exciting and relaxing at the same time. The most awesome feeling I had ever had in my life.
Lee had stopped playing with himself while I had my orgasm and grabbed his briefs and handed them to me to clean up. My cum was mostly clear with streaks of white in it and smelled funny but arousing at the same time, if that makes sense. I marvelled at it's slimy, sticky consistency and found that the head of my penis was extremely sensitive as I wiped myself off and I flinched, startled. Lee said that was normal but to be careful for a few minutes.
He then said "My turn" and re-lubed himself and used his whole hand to stroke himself. It didn't take him but a minute or so and he too lay back on the bed as I watched, his hips bucking like mine had. I noticed his nuts pull up to his body and he started shooting all over his stomach and chest. A lot more than I had and it was all white compared to mine. He sighed and had a smile on his face and said "Man, that always feels soooooooo good".
He grabbed his briefs and wiped himself off and threw them on our pile of dirty clothes. I was a bit concerned our Mom would notice, his briefs were covered in our cum, and I said so. He said when he started jacking off he used a sock to clean up and would leave it under the bed to use again but she said to just put whatever he used with the dirty clothes every time he did it so it was no big deal. I was kind of stunned our mother knew what he was doing and he said at first he was embarrassed but she said it was normal and not to worry about it.
I asked how often you could do this and he laughed and said we could do it again right now if we wanted but he usually did it once a day, sometimes twice. And now he wouldn't have to wait for me to fall asleep. He then put the lotion on the small night stand between our beds so we could both use it. Curious, I asked how he learned how to do this and he told me never to mention it to him but his friend ..... showed him how. Then he seemed to have a thought and said maybe it would be a good idea if I told my buddy Dan how to do it since he was an only child. I'd already thought I'd share my new found knowledge with Dan and agreed.
So, that's how I learned how to masturbate. I'm glad my parents were aware what boys go through when growing up and weren't prudes. I thanked my Dad for having Lee show me the ropes and my Mom was always sure to get us another bottle of lotion when ours ran dry. When my younger brother John started puberty my Dad mentioned maybe I should teach him like Lee had taught me but when I brought the subject up to John he had already figured it out for himself but thought it was something no-one had done before. But he didn't think about using some kind of lube other than his own spit and was happy when I told him about using hand lotion.
My next story will be about my best friend Dan and I and how I taught him.