Where it happened: my room.
Langauge: english.
Sex: Female
Rating: 5
Category: Straight
I had been dating a boy for about two months, but we had liked each other and tried to date for about a year and it never really worked out. We knew we wanted to have sex, but it was a matter of us being too busy and never alone long enough for it to happen, and if we were alone long enough, we could never gather the nerve to go for it because we were nervous since neither of us had done it before. One morning he came over before school, just to hang out, and he sat down on my piano bench. I went behind him and wrapped my arms around him and told him I had to get dressed and he could come up to my room with me. He sat down on my bed and I kissed him, then pushed him down so I was laying on top of him. He seemed pretty stoked about it, so we started making out. He rolled over on top of me and kicked off his shoes and pulled off his jacket. I got under my covers and I pulled him under with me. He unzipped my hoodie, which was all I was wearing besides a pair of shorts because that’s what I had slept in that night, and he put his hand down my shorts to finger me. At that point I had decided that I wasn’t nervous anymore and I wanted to go for it. I pulled his shirt off and started to unzip his pants when he told me he had left his condoms at home. Then I reminded him that I kept one in my car, so he put his clothes back on and went outside to get it. When he came back, I undressed him really fast and we got back under the covers and he put the condom on. He got on top of me and tried to penetrate me, but I was too tight so I cringed away because it hurt too much. He said that if I got on top it might be easier, so we switched positions and it did help. He could only go about halfway in because I would cringe if he went any further, and he didn’t want to hurt me. We kept at it, and he finished a few minutes later, which I really didn’t mind because I was in a lot of pain. I told him that I loved him, the first time I had ever said it outloud (not in a note or a text), and he said he loved me too, and he kissed me. It was a slightly awkward experience, but it was perfect, and I wouldn’t have wanted my first time to be any different.
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