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Once upon a time, A boy named Clay from school bought me ice cream. He bought me ice cream and we hung out together. Everyone teased us and said we were dating but it wasn’t like that for me. Eventually, Clay asked me to a middle school dance and never showed up. Because his parents wouldn’t drive him. After that, I got mad at him and I wouldn’t talk to him. He thought I was a lot madder than I actually was and although we still kind of talked, I got a boyfriend. I loved my boyfriend more than anything in the world and when he left me I tried to kill myself. I lived and moved away to go to college.

Clay eventually got the guts to talk to me again. We started going to the movies, going to dinner, and hanging out like we used to. Eventually, he leads on that he wanted to be more than my friend. It started as us just watching Tv in my apartment, he jokingly asked if I wanted to make out and I said sure! and gave him a big exaggerated kiss on the lips as a joke. He told me it was his first one and I felt so bad so I gave him two real ones.
The next time we met up it was more than just kisses, we ended up half naked in my bed and he wanted to have s**. I said no, I didn’t want to. He understood.

A couple of weeks later, he came to see me for Valentine’s day and I ended up losing my virginity to him. I didn’t mind. He was sweet to me and had once told me he had liked me since preschool. But not even 10 minutes after we were done he broke up with me. He said the hour long drive to see me was too much, and how they were promoting him to the manager position. I told him I understood. A few weeks later I thought I was pregnant and reached out to him. He never answered a single text.

Although luckily the test was negative,
My heart is broken and I wish he would talk to me.

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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.