I have had several experiences with masturbation. I started masturbating after an encounter with a female friend at the age of ten.
This girl was thirteen and the daughter of my mother's friend and actually quite a tomboy. We had played football for most of the day and were ready to settle down and just 'hang out'. We went inside and decided to watch television for a while before she was to go home. It turned out we had got into a few movies and she was going to stay the night.
At the time, I had no intentions of this evening becoming sexual, after all I was only ten. We were up all night watching TV and my mother had gone to sleep. We were quite bored and then (like many kids do at this age) decided to play a little truth or dare. It started off innocent then quickly progressed to become awfully sexual.
It started by her asking if I had any pubic hair. I replied no and she laughed. I assumed she hadn't any either so I told her so. However when she pulled down her pants slightly to show me a thick bush, I was inclined to believe otherwise.
From there I dared her to show me her pussy. She initially declined but eventually did. That led to me showing her my small ten-year-old dick, which was quickly becoming hard.
At this point, she said she wanted to show me a trick. She left the room but soon returned with some ice cubes. She then removed her shirt and bra (which encased an amazing set of 34b breasts) and proceeded to put the ice cubes on her nipples and move them in circles, allowing these amazing little marbles to be quite hard. She could tell I was into this and told me it was ok that I could touch them. I did so willingly and then proceeded to place my lips to her nipples and kissed them. She told me to then lick and suck them. She let out a few moans and then backed away. She told me to take off my pants and try to cum.
I had no clue what she was talking about. But she soon showed me. She took her hand and placed it on my now rock hard prick. She started jacking me off. I just laid back and enjoyed. After a while I got up the courage to play with her breasts while she was slowly playing with my cock. I tugged at her nipples and squeezed her breasts.
Then the most amazing thing happened she took off her pants and underwear and started to play with her clit while she jerked me off with her other hand. I had no idea what she was doing, but it looked like she was enjoying it. As her hand moved faster on my cock her other hand moved quicker on her pussy.
Soon though, I was no longer paying attention to what she was doing to herself and focused on what she was doing to me. I could feel this amazing sensation boiling up inside me and soon it hit. I felt a pulse of pleasure fly through my entire body. At the same time her strokes stopped and she was throwing her head back and arching her back, forcing her pussy into her hand. She let out a muffled moan and then laid back in a daze.
I leaned over and asked her what I had just felt. She told me it was an 'orgasm'. We were both tired and decided it was time to go to bed. Nothing like that ever happened again. She went off to the middle school while I was still stuck in grade school.
This served though as the catalyst for all my masturbation experiences. I plan on submitting a few more stories on here if you all are interested.