7 years
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the first time I had s** was when I was 12 years old. There was this retarded woman in my neighborhood that a few older guys fucked. Most kids my are made fun of her and teased her but I got along with her and used to talk to her a lot. One day, we were sitting on her front porch and I asked her if she wanted to do it. We went up to the woods and she told me I could do whatever I wanted except for in the b*** because that hurts. I had her s*** on my c*** and then had her lay down on the ground with her shorts pulled down and I got on top of her and after trying for a while, I slid inside of her. It was warm. I pumped like 7 or 8 times and climaxed. I was too young to shoot a load but I did climax. I remember seeing her p**** before I got on top of her. she spread it apart and it was not pink like the ones I saw in the magazines. It was a light purple instead. I never told anyone about this before. I lost my virginity when I was 12 to a 32 year old retarded woman.

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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.