This was my first time and it was by accident!
I have never written anything like this before, but here it goes. This happened when I was 13, and I had gone to stay at my grandparents house for one week. They lived two hours away, and I was going to stay in the attic bedroom, which was very large, but didn't have airconditioning, just a fan.
Like many 13 year olds, I was aching to know how it was to be with a woman, and I was constantly horny. I had previously had two wet dreams, but knew nothing about masturbation.
One night like always, I took my bath and went upstairs to go to bed, but I was terribly horny. I left the night light on, and turned on the fan. The good thing about the attic was complete privacy. So, I slid off my underwear, and started looking at my purple headed penis, which immediately became erect. I was so horny, that I started to tremble and my mouth went dry. I started touching myself, and looking at my erection in the mirror, and then I got an idea. What was it like to be inside a woman? I quickly thought of putting the two pillows on top of each other and then sliding my penis inside, to see how it felt. My heart was in my throat-this was so incredible. I laid the pillows on top of each other and crawled on the bed. Then slowly I slid inside. The reaction was both unexpected, and incredible. My body lurched forward, and I gasped involuntarily, and my whole body spasmed, and my face became red hot at the same time-I emptied my precious cream in between the two pillows, not knowing what was going on, but the feeling was so incredible!
After I came, I looked between the pillows, and the musky smell of semen hit my nose, and I felt dizzy. I touched the cum and actually tasted it, I still wasn't sure what it was, but after a few minutes I figured everything out.
What a feeling! After that I did it every night that week, and always looked forward to my special room at my grandparents house every time I went for a weekend, or a holiday.