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The first time I tried to have sex was with my first serious boyfriend, whom I thought I'd be with the rest of my life... well we planned it and we really wanted to do it, or at least I wanted too, I wanted to be with my friends who already lost their virginity. So we took a blanket and went way out into the woods next to a river and we placed the blanket down and started stripping each other. I had seen photos of his dick so seeing him naked for the first time wasn't as big of a shocker. I felt confident that I could do it. We were both virgins but we thought we had the experience from watching animé porn, apparently not because he had a hard time finding where to insert his penis. Finally as I showed him we were getting really close to losing our virginity until I pushed away because it hurt like hell, like as if someone was ripping my vagina open and shoving knifes into it hell. I didn't let him get close to me it was nothing what I had expected. So we didn't do it.
Then we broke up because I found out he only wanted me for the sex and I was refusing to give it to him. I cried for days after we broke up...
Well I tried it again a few months later with a different boy, he wasn't my boyfriend and we made sure that we both weren't cheating, just too single people having sex. I had been talking to him through text, he goes to my school and every once in a while we would sneak off at lunch somewhere private and start making out and he'd get his hand in my pants and invade me body. Well I ditched 2nd period to go walk to his house because he decided to drop out of school, and I knew we were gonna end up having sex because we had been planning to do it for a long time. I waited for his sister to leave so we could have his house to ourselves. He was a virgin too but he acted like he knew what he was doing, he started taking my clothes off and taking his clothes off and eventually I was sitting on the couch with him up against me, at first I backed away because it really hurt then he convinced me and we started doing it, we started having sex, and that is how I lost my virginity.
though once I left his house to go back to school I started freaking out on the inside and when I got home I started crying for hours... painful but in a way I was glad I got it over with.