13 years
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When I was age 7 or 8 I didn’t know what m*********** was. The closest thing I had was getting naked and getting into a sleeping bag with my biggest stuffed animal, though obviously that didn’t really do anything for me. I was curious about s** from a young age. When I was 5 and 6 my best friend was the girl next door. We would play like normal kids, but also make out a lot. When I was 9 I had to spend most of the summer with my grandmother while my mom was at work. I was getting out of the shower one day and noticed a bottle of lotion by the sink. I put the lotion on my p****, I don’t know why I did it, and suddenly I felt amazing. I pulled my pork until I finished. Though at that young age nothing actually came out, I still had an o*****. This was the single greatest discovery of my life. From that day forward I masturbated virtually every day of my life. By my modest calculations I have masturbated well over 4,000 times. When I was 12 and 13 it was the worst. One night I had a friend sleep over and when he fell asleep I spanked it with him lying right by me. If I started jerking I had to finish. Sometimes it would take me as long as an hour. I often did it in the shower, so this wasted a lot of water. One day I walked home from school and it was raining really heavily. I realized that I left my keys in the house and no one was home. I had nothing else to do, so I played with myself while I waited by the back door. Just as I finish my grandmother comes and opens the door to let me in. I hid my shame underneath my old navy pullover and hoped that she didn’t see anything. If she did, she pretended not to.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.