7 years
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I thought my first time would be magical like the books all tell you. It was nothing romantic. I mean sure, we were both hot and into the passion, but when he put it inside of me, it hurt so bad, I couldn’t think of anything else but how bad it was hurting. I almost told him to stop but I didn’t because I love him and I know he liked it. I made him wait 17 months. It only lasted a few minutes and about the time the pain was stopping, he was stopping too. He tensed up for about 10 seconds and then started breathing heavy and then relaxed. I got really really wet too. I am guessing that was him c******. I thought I would bleed a ton, but when I went into the bathroom and wiped, there was a few drops of blood and nothing more. I have seen p*** movies and they do it for like 15-45 minutes before he cums. WTF? S** is not it is all cracked up to be. I am sure we will be doing it again. I guess I should look into getting on the pill or something now that I am a woman. I just hope it gets better. I hope it doesn’t hurt like that every time.

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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.