I am relating the two most memorable experiences in regard to masturbation, two that I reference frequently even now, and I am 56 years old. The first occurred with my sister who is almost than 5 years older than me. I was nine, in fourth grade and she was in eighth and it was a day off from school and it was snowy and dull. She told me she was going to take a nap and not to come in her room because she wasn't going to wear any clothes. That was all I needed to get me to do the opposite, so about a half hour later, I tried her door, expecting it to be locked but it wasn't. There she was, laying on her back, her little tits swayed slightly out to her sides, the orange-pink nipples protruding in points that looked very interesting. Her knees were up and apart and her right hand was resting on her crotch, her middle finger slightly inserted into the dimpled lip-like line of her peehole as she slept. It made me feel funny to see her and my peter started to become stiff in my pants. As I watched her she moved her finger and hips, her fingertip disappearing and reappearing as she did so. Then she moved again, opening her legs even further as she took her hand away. I was feverish by now and I stood right next to her, looking at her pussy until I decided to touch her down there. I put my first two fingertips against the slight opening of her pussy lips and pushed them in. Her skin down there was slippery and I liked how it felt. My fingertips wiggled up and down pushing in as I rubbed her, and I could feel my peter tingling and itching like nothing I had ever felt before. My sister moaned and moved her bottom so she was moving with my fingers and I jumped when she moved. But she was just putting her hands up to her tits, touching her nipples and pulling them so they really stuck out, her eyes still shut tight. After about two minutes, my cock felt like it was exploding in my pants, a feeling that made me weak because it felt so good. About a minute later, my sister moaned and lifted up on the bed and I could feel her flesh throbbing against my fingers. A few seconds later she rolled sideways, closing her knees and putting her arm across her tits. I was on fire, and I moved to the other side of the bed. I could see her reddened and puffy pussy from the back, right below her ass crack. I reached out and started to touch again, rubbing the slipperiness all around her pussy and her asshole and pushing my fingers into her pussy from the back. I took out my cock and held it in my left hand while I rubbed her with my right. I was rubbing myself with my hand and that feeling along it started to build up again. Again about two minutes later that wonderful feeling throbbed through my cock a second time. Nothing came out but the feeling was sensational. My cock softened but I still kept pushing my two fingers in and out of my sisters pussy from the back, until I finally must have got a bit carried away and went too far in. She rolled over and covered herself up and said 'I told you not to come in here, you little brat! Get out or I'm going to tell mom'. She never told on me, and we never ever did anything like that again. But I spent lots of time rubbing my cock and thinking about it. I was in sixth grade the first time I ever ejaculated and that only added to my interest. My record was seven times in one day before I started to slack off.
The other most memorable was when I was in eighth grade. I still jerked off frequently, but like most kids then, was still a virgin. I was one of the eighth grade bad boys and one day we were hanging out and tossing a football after school and I needed to take a leak. We weren't supposed to go back in school but I went in and up to the boys restroom. It had a 'closed' sign on the floor in front of the door, but I went in anyway and stepped up to the urinal and unzipped and was reaching in my fly. Right then, out of one of the stalls comes Sister Lucy, this older nun who taught 3rd and 4th grades, holding a toilet brush, her habit tucked up in her belt in front like the nuns did when they were cleaning in the school, exposing her black stocking-clad legs. 'What are you doing in here?' she asked harshly, pointing at me with the toilet brush. 'You aren't supposed to be in this building after school hours!' I told her I was sorry but I had to use the bathroom and thought it would be all right. Glaring at me, she told me to go ahead. Having been conditioned to do what the nuns told us, I stepped back to the urinal and took out my cock, which was becoming thicker and thicker and stiffer and stiffer as she stood at my side, watching me. I was totally erect in seconds, my full almost five inches pointing up in the air under the stern gaze of Sister Lucy. I bent it down and tried to piss but it wasn't going to work out, not with her watching me. 'Well! I thought you had to use the restroom! Go!' I was getting nervous and I said, 'I can't Sister. Something is wrong with my thing. Its all hard and I can't go'. I felt weak as she took my shoulder and turned me toward her, my cock sticking up almost straight up. She took my cock in her hand and said, 'yes, it IS very hard. Now, I can show you how to fix it but you must promise to never tell anyone. Will you do that?' 'Yes Sister!' I agreed quickly. She squeezed my cock and rubbed her thumb against the tip, making the pre-come bead out from its opening. She swirled the clear juice around the tip and down the front of my cock and believe me it felt good! Nobody else had ever touched my cock and here was this nun, her robe lifted up and hanging at mid-thigh, jerking me off. Then she knelt down and her hand moved slowly as she stared at my cock, moving the skin against its inner rigidity, up over the tip and back, again and again but only for about a half minute before my knees weakened and I came with unbelievable force, squirting the first jet of come over her shoulder to land on the wall before she covered the tip with her hand and let the rest of my come squirt against it, rubbing the slippery coating over my cock with her hand. I finally softened to a semi-dangle, but Sister still knelt, looking at my cock with a glazed look. I was starting to think she was going to blow me, hoping on hope that it was going to happen. But finally, she got to her feet, her face flushed and her breath very uneven, her hand still thickly coated with my come. Her voice sounded strange as she told me 'Now go to the bathroom. And never come in here after school again'. She went back in the stall as I stood at the urinal for a time long enough for it to seem like I went, then flushed and left.
Is it any wonder that these experiences can still make me jerk off?